METHOD FOR PRODUCING AMINO ACID AMINOALKYL ESTER OR INORGANIC ACID SALT THEREOF

Abstract

The present invention provides a method for producing an amino acid aminoalkyl ester or an inorganic acid salt thereof by reacting a compound represented by general formula (I) shown below or a compound represented by general formula (III) shown below, or a salt thereof, and at least one compound selected from the group consisting of compounds represented by general formula (IV-I) shown below, compounds represented by general formula (IV-II) shown below, compounds represented by general formula (IV-III) shown below and compounds represented by general formula (IV-IV) shown below, or an inorganic acid salt thereof.

##STR00001##

Claims

1. A method for producing an amino acid aminoalkyl ester or an inorganic acid salt thereof by reacting: a compound represented by general formula (I) shown below or a compound represented by general formula (III) shown below, or a salt thereof, and at least one compound selected from the group consisting of compounds represented by general formula (IV-I) shown below, compounds represented by general formula (IV-II) shown below, compounds represented by general formula (IV-III) shown below and compounds represented by general formula (IV-IV) shown below, or an inorganic acid salt thereof: ##STR00207## (wherein in general formula (I), R.sup.11 represents a hydrogen atom, a monovalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms which may have a substituent, or a monovalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms which may have a substituent; the substituent is at least one group selected from the group consisting of monovalent aliphatic hydrocarbon groups of at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups of at least 6 but not more than 10 carbon atoms, halogeno groups, alkoxy groups, thioalkyl groups, a primary amino group (—NH.sub.2), a carboxyl group, a carbamide group (—NHCONH.sub.2), groups represented by general formula (II-1) shown below, groups represented by general formula (II-2) shown below, groups represented by general formula (II-3) shown below, and groups represented by general formula (II-4) shown below; R.sup.12 represents at least one group selected from the group consisting of an amino group, a carbamide group (—NHCONH.sub.2), groups represented by general formula (II-1) shown below, groups represented by general formula (II-2) shown below, and groups represented by general formula (II-3) shown below; R.sup.13 represents a hydrogen atom or an n11-valent organic group; and n11 is an integer of at least 1 but not more than 4), ##STR00208## (wherein in general formula (II-1), R.sup.21 represents a monovalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms which may have a substituent, or a monovalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms which may have a substituent; in general formula (II-2), R.sup.22 represents a monovalent organic group; in general formula (II-3), each of R.sup.23 and R.sup.24 independently represents a monovalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms which may have a substituent, or a monovalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms which may have a substituent; and in general formula (II-4), R.sup.25 represents a hydrogen atom or a monovalent organic group), ##STR00209## (wherein in general formula (III), n31 is an integer of at least 2 but not more than 4; R.sup.31 represents an n31-valent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms which may have a substituent, or an n31-valent aromatic cyclic group of at least 6 but not more than 10 carbon atoms which may have a substituent; the substituent is at least one group selected from the group consisting of monovalent aliphatic hydrocarbon groups of at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups of at least 6 but not more than 10 carbon atoms, halogeno groups, alkoxy groups, thioalkyl groups, a primary amino group (—NH.sub.2), a carboxyl group, a carbamide group (—NHCONH.sub.2), groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4); R.sup.32 represents at least one group selected from the group consisting of an amino group, a carbamide group (—NHCONH.sub.2), groups represented by the general formula (II-1), groups represented by the general formula (II-2), and groups represented by the general formula (II-3); and R.sup.33 represents a hydrogen atom or a monovalent organic group), ##STR00210## (wherein in general formula (IV-I), Y.sup.401 represents a divalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms; and R.sup.401 represents at least one group selected from the group consisting of an amino group, a carbamide group (—NHCONH.sub.2), groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4)), ##STR00211## (wherein in general formula (IV-II), each of Y.sup.402 and Y.sup.403 independently represents a divalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms; and each of R.sup.402 and R.sup.403 independently represents at least one group selected from the group consisting of a hydrogen, an amino group, a carbamide group (—NHCONH.sub.2), groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4)), ##STR00212## (wherein in general formula (IV-III), each of Y.sup.404, Y.sup.405 and Y.sup.406 independently represents a divalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms; and each of R.sup.404, R.sup.405 and R.sup.406 independently represents at least one group selected from the group consisting of a hydrogen, an amino group, a carbamide group (—NHCONH.sub.2), groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4)), ##STR00213## (wherein in general formula (IV-IV), each of Y.sup.407, Y.sup.408, Y.sup.409 and Y.sup.4010 represents a divalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms or a divalent aromatic cyclic group of at least 6 but not more than 10 carbon atoms; at least one of R.sup.407, R.sup.408, R.sup.409 and R.sup.4010 represents a hydroxyl group, and each of the others represents at least one group selected from the group consisting of a hydrogen, an amino group, a carbamide group (—NHCONH.sub.2), groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4)).

2. The method according to claim 1, wherein the reaction is conducted in presence of at least one acid catalyst selected from the group consisting of organic acids and inorganic acids having a normal boiling point of 0° C. or higher.

3. The method according to claim 1, wherein the compound represented by the general formula (I) is at least one amino acid selected from the group consisting of lysine, glutamic acid, methionine, glycine, phenylalanine, asparagine, alanine, leucine, isoleucine, and valine.

4. The method according to claim 2, wherein the inorganic acid used as an acid catalyst is at least one acid selected from the group consisting of sulfuric acid, phosphoric acid, nitric acid and boric acid.

5. The method according to claim 2, wherein an acid that forms a salt with the compound represented by general formula (I) or the compound represented by general formula (III) and the acid catalyst are the same acid.

6. The method according to claim 1, wherein in the general formula (I): the substituent is at least one group selected from the group consisting of monovalent aliphatic hydrocarbon groups of at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups of at least 6 but not more than 10 carbon atoms, groups represented by the general formula (II-1), and groups represented by the general formula (II-2), R.sup.12 is a group represented by the general formula (II-1) or a group represented by the general formula (II-2), R.sup.13 is a hydrogen atom, and n11 is 1; and in the general formula (III): the substituent is at least one group selected from the group consisting of monovalent aliphatic hydrocarbon groups of at least 1 but not more than 10 carbon atoms, monovalent aromatic cyclic groups of at least 6 but not more than 10 carbon atoms, groups represented by the general formula (II-1), groups represented by the general formula (II-2), groups represented by the general formula (II-3), and groups represented by the general formula (II-4), and R.sup.32 is at least one group selected from the group consisting of groups represented by the general formula (II-1), groups represented by the general formula (II-2), and groups represented by the general formula (II-3).

7. The method according to claim 1, wherein the compound represented by general formula (I) or the compound represented by general formula (III), or a salt thereof, is reacted with the compound represented by general formula (IV-I) or an inorganic acid salt thereof.

8. The method according to claim 7, wherein in the general formula (I): R.sup.11 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms which may have a substituent, the substituent is a group represented by the general formula (II-1), R.sup.12 is a group represented by the general formula (II-1), and R.sup.13 is a hydrogen atom; and in the general formula (IV-I): Y.sup.401 is a divalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms, and R.sup.401 is a group represented by the general formula (II-1).

9. The method according to claim 2, wherein the acid catalyst is included in an amount of 1 ppm to 5% by mass.

10. The method according to claim 6, wherein the compound represented by general formula (I) or the compound represented by general formula (III), or a salt thereof, is reacted with the compound represented by general formula (IV-I) or an inorganic acid salt thereof.

11. The method according to claim 10, wherein in the general formula (I): R.sup.11 represents a hydrogen atom or a monovalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms which may have a substituent, the substituent is a group represented by the general formula (II-1), R.sup.12 is a group represented by the general formula (II-1), and R.sup.13 is a hydrogen atom; and in the general formula (IV-I): Y.sup.401 is a divalent aliphatic hydrocarbon group of at least 1 but not more than 10 carbon atoms, and R.sup.401 is a group represented by the general formula (II-1).

Description

EXAMPLES

[0238] Embodiments of the present invention are described below in further detail using specific examples, but the embodiments of the present invention are in no way limited by the following examples, provided they do not exceed the scope of the invention.

[Synthesis Example 1] Synthesis of Compound (A-20)

[0239] A glass flask with an internal capacity of 500 mL was charged with 200 g of lysine monohydrochloride, 34 g of urea and 100 g of water, and the resulting mixture was heated at 120° C. for 2 hours while being stirred under a nitrogen atmosphere at atmospheric pressure. The reaction liquid was then cooled, the reaction liquid was poured into 2-propanol, and the precipitated solid was collected by filtration. Analysis by .sup.1H-NMR revealed that the collected solid was a compound in which the amino group of the lysine had been substituted with a urea linkage. This compound was used as compound (A-20) as a raw material in Example 22 described below.

[Example 1] Production of Compound (E-1)

[0240] A glass flask with an internal capacity of 1,000 mL fitted with a distillation device was charged with 200 g of a compound (A-1) (glycine) shown as the raw material 1 in Table 1 below, 171 g of a compound (B-1) (ethanolamine) shown as the raw material 2 in Table 1 below, 200 g of toluene and 214 g of phosphoric acid, and a reaction was conducted under reduced pressure at 100° C., with the toluene being distilled off while additional toluene was added to keep the liquid level substantially constant. After continuing the reaction for 8 hours, collection of the reaction liquid and analysis by liquid chromatography revealed that a compound (E-1) shown as the product in Table 1 below had been produced at a yield of 84% relative to the amount added of the compound (A-1) (glycine). Analysis of the amount of phosphoric acid contained in the compound (E-1) (excluding the counter anion component) by a conventional method revealed 350 wtppm of phosphoric acid relative to the compound (E-1).

[Examples 2 to 48] Production of Compound (E-2) to Compound (E-48)

[0241] With the exceptions of adding the raw material 1, the raw material 2 and the solvent in the combinations shown below in Tables 1 to 8, and setting the reaction temperature, pressure and time as shown below in Tables 1 to 8, the same method as Example 1 was used to produce compounds (E-2) to (E-48).

Comparative Example 1

[0242] With the exception of replacing the acid used in Example 9 from phosphoric acid to hydrogen chloride, a reaction was conducted using the same method as Example 9. The method for supplying the hydrogen chloride involved supplying hydrogen chloride gas from a hydrogen chloride cylinder using a flow meter that used a corrosion-resistant material of stainless steel or glass, introducing the hydrogen chloride gas into the reaction system while controlling the supply rate and conducting the reaction by bubbling the gas through the liquid phase, and following completion of the reaction, calculating the amount of hydrogen chloride gas introduced into the system to calculate the weight of hydrogen chloride supplied. In this reaction, the yield of the produced compound (E-9) was 55%.

Comparative Example 2

[0243] With the exception of replacing the acid used in Example 10 from methanesulfonic acid to hydrogen chloride, a reaction was conducted using the same method as Example 10. The hydrogen chloride was supplied to the reaction system using the same method as Comparative Example 1. In this reaction, the yield of the produced compound (E-10) was 50%.

TABLE-US-00001 TABLE 1 Raw material 1: Raw material 2: Compound (I) or Compound (II) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount Mole- ount Mole- Com- ount Com- Structural added cular Com- Structural added cular molar pound added Examples pound formula (g) weight pound formula (g) weight ratio name (g) Example 1 A-1 [00053] 200  75 B-1 [00054] 170  61 0.96 phos- phoric acid 214 Example 2 A-1 [00055] 200  75 B-2 [00056] 430 159 0.99 phos- phoric acid 210 Example 3 A-2 [00057] 200  75 B-2 [00058] 430 159 0.99 phos- phoric acid 210 Example 4 A-3 [00059] 200  75 B-2 [00060] 430 159 0.99 phos- phoric acid 210 Example 5 A-4 [00061] 200  89 B-1 [00062] 143  61 0.96 phos- phoric acid 180 Example 6 A-4 [00063] 200  89 B-1 [00064] 143  61 0.96 sulfuric acid 270 Example 7 A-5 [00065] 150 297 B-3 [00066] 119  75 0.32 p- toluene sulfonic acid 432 Am- ount Solvent Reaction of acid Am- conditions in Com- ount Temp- Pres- Product pro- pound added erature sure Time Com- Structural Yield duct Examples name (g) (° C.) (kPa) (hr) pound formula (%) wt % Example 1 toluene 200 100 80  8 E-1 [00067] 84 0.05 Example 2 toluene 200 100 80 10 E-2 [00068] 82 0.03 Example 3 toluene 200 100 80 10 E-3 [00069] 82 0.08 Example 4 toluene 200 100 80 10 E-4 [00070] 82 0.06 Example 5 toluene 200 100 80  8 E-5 [00071] 78 0.04 Example 6 toluene 200 100 80  8 E-6 [00072] 76 0.08 Example 7 o- dichloro benzene 100 110 10  6 E-7 [00073] 68 0.06 [00074]

TABLE-US-00002 TABLE 2 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount Mole- ount Mole- Com- ount Com- Structural added cular Com- Structural added cular molar pound added Examples pound formula (g) weight pound formula (g) weight ratio name (g) Example 8 A-6 [00075] 150 201 B-4 [00076]  57 148 1.94 tri- fluoro- meth- ane sul- fonic acid 134 Example 9 A-7 [00077] 200 182 B-1 [00078]  70  61 0.96 phos- phoric acid 130 Example 10 A-8 [00079] 150 223 B-5 [00080] 120 181 1.01 meth- ane sul- fonic acid 277 Example 11 A-9 [00081] 150 113 B-5 [00082] 120 181 1.01 meth- ane sul- fonic acid 277 Example 12 A-10 [00083] 300 178 B-4 [00084] 121 148 2.06 phos- phoric acid  46 Example 13 A-11 [00085] 130 147 B-6 [00086] 181  97 0.47 phos- phoric acid 348 Example 14 A-12 [00087] 300 207 B-7 [00088] 138 101 1.06 sul- furic acid 147 Am- ount Solvent Reaction of acid Am- conditions in Com- ount Temp- Pres- Product pro- pound added erature sure Time Com- Structural Yield duct Examples name (g) (° C.) (kPa) (hr) pound formula (%) wt % Example 8 o- di- chloro ben- zene 200 110 10  8 E-8 [00089] 73 0.04 Example 9 toluene 200 100 80  8 E-9 [00090] 79 0.05 Example 10 toluene 200 100 80  8 E-10 [00091] 73 0.06 Example 11 toluene 200 100 80  8 E-11 [00092] 73 0.07 Example 12 xylene 300 130 40  5 E-12 [00093] 83 0.06 Example 13 xylene 100 130 40  8 E-13 [00094] 79 0.04 Example 14 toluene 200 100 80 10 E-14 [00095] 78 0.08 [00096]

TABLE-US-00003 TABLE 3 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount ount ount add- Mole- add- Mole- Com- add- Com- Structural ed cular Com- Structural ed cular molar pound ed Examples pound formula (g) weight pound formula (g) weight ratio name (g) Example 15 A-13 [00097] 200 187 B-8 [00098] 179 181 1.08 sul- furic acid 106 Example 16 A-14 [00099] 200 442 B-5 [00100] 135 181 0.61 phos- phoric acid 181 Example 17 A-15 [00101] 300 386 B-5 [00102] 135 181 1.04 phos- phoric acid 181 Example 18 A-16 [00103] 150 231 B-9 [00104] 114 160 0.91 phos- phoric acid 173 Example 19 A-17 [00105] 150 204 B-4 [00106] 239 148 0.46 phos- phoric acid  46 Example 20 A-18 [00107] 150 205 B-7 [00108]  78 101 0.95 meth- ane sul- fonic acid  40 Example 21 A-19 [00109] 200 175 B-8 [00110] 143 147 1.17 phos- phoric acid 180 Example 22 A-20 [00111] 150 — B-5 [00112] 103 181 1.1  rel- ative to car- boxy phos- phoric acid 139 Am- ount of Solvent Reaction acid Am- conditions in Com- ount Temp- Pres- Product pro- pound added erature sure Time Com- Structural Yield duct Examples name (g) (° C.) (kPa) (hr) pound formula (%) wt % Example 15 toluene 200 100 80 10 E-15 [00113] 79 0.05 Example 16 toluene 200 100 80 10 E-16 [00114] 80 0.06 Example 17 toluene 200 100 80 10 E-17 [00115] 81 0.07 Example 18 xylene 300 130 40  5 E-18 [00116] 82 0.06 Example 19 xylene 200 130 40  5 E-19 [00117] 81 0.04 Example 20 toluene 200 100 80  8 E-20 [00118] 79 0.03 Example 21 toluene 200 100 80  8 E-21 [00119] 80 0.04 Example 22 toluene 200 100 80 10 E-22 [00120] 81 0.05 [00121]

TABLE-US-00004 TABLE 4 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount ount ount add- Mole- add- Mole- Com- add- Ex- Com- Structural ed cular Com- Structural ed cular molar pound ed amples pound formula (g) weight pound formula (g) weight ratio name (g) Ex- ample 23 A-21 [00122] 150 260 B-5 [00123] 103 181 1.01 phos- phoric acid 139 Ex- ample 24 A-21 [00124] 200 386 B-9 [00125]  41  75 0.95 phos- phoric acid 139 Ex- ample 25 A-21 [00126] 200 386 B-10 [00127]  48  89 0.96 phos- phoric acid 139 Ex- ample 26 A-21 [00128] 200 386 B-11 [00129]  35 330 4.88 phos- phoric acid 139 Ex- ample 27 A-21 [00130] 200 386 B-12 [00131]  50 479 4.96 phos- phoric acid 139 Am- ount Solvent Reaction of acid Am- conditions in Com- ount Temp- Pres- Product pro- pound added erature sure Time Com- Structural Yield duct Examples name (g) (° C.) (kPa) (hr) pound formula (%) w % Example 23 toluene 200 100 80 10 E-23 [00132] 80 0.06 Example 24 o- dichloro benzene 100 110 10  6 E-24 [00133] 79 0.04 Example 25 o- dichloro benzene 100 110 10  6 E-25 [00134] 78 0.04 Example 26 o- dichloro benzene 100 110 10  6 E-26 [00135] 77 0.05 Example 27 o- dichloro benzene 100 110 10  6 E-27 [00136] 78 0.06

TABLE-US-00005 TABLE 5 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount ount ount add- Mole- add- Mole- Com- add- Ex- Com- Structural ed cular Com- Structural ed cular molar pound ed amples pound formula (g) weight pound formula (g) weight ratio name (g) Ex- ample 28 A-21 [00137] 200 386 B-13 [00138] 75 493 3.40 phos- phoric acid 139 Ex- ample 29 A-21 [00139] 200 386 B-9 [00140] 41  75 0.95 p- tol- uene sul- fonic acid 432 Ex- ample 30 A-21 [00141] 200 386 B-10 [00142] 48  89 0.96 p- tol- uene sul- fonic acid 432 Ex- ample 31 A-21 [00143] 200 386 B-11 [00144] 35 330 4.88 p- tol- uene sul- fonic acid 432 Ex- ample 32 A-21 [00145] 200 386 B-12 [00146] 50 479 4.96 p- tol- uene sul- fonic acid 432 Am- ount Solvent Reaction of acid Am- conditions in Com- ount Temp- Pres- Product pro- Ex- pound added erature sure Time Com- Structural Yield duct amples name (g) (° C.) (kPa) (hr) pound formula (%) wt % Ex- ample 28 o- dichloro benzene 100 110 10 6 E-28 [00147] 76 0.07 Ex- ample 29 o- dichloro benzene 100 110 10 6 E-29 [00148] 77 0.06 Ex- ample 30 o- dichloro benzene 100 110 10 6 E-30 [00149] 79 0.05 Ex- ample 31 o- dichloro benzene 100 110 10 6 E-31 [00150] 75 0.04 Ex- ample 32 o- dichloro benzene 100 110 10 6 E-32 [00151] 74 0.06

TABLE-US-00006 TABLE 6 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount ount ount add- Mole- add- Mole- Com- add- Ex- Com- Structural ed cular Com- Structural ed cular molar pound ed amples pound formula (g) weight pound formula (g) weight ratio name (g) Ex- ample 33 A-21 [00152] 200 386 B-13 [00153] 75 493 3.40 p- tol- uene sul- fonic acid 432 Ex- ample 34 A-21 [00154] 200 386 B-14 [00155] 41  75 0.95 p- tol- uene sul- fonic acid 432 Ex- ample 35 A-21 [00156] 200 386 B-15 [00157] 48 89 0.96 p- tol- uene sul- fonic acid 432 Ex- ample 36 A-21 [00158] 200 386 B-16 [00159] 35 330 4.88 p- tol- uene sul- fonic acid 432 Ex- ample 37 A-21 [00160] 200 386 B-17 [00161] 50 479 4.96 p- tol- uene sul- fonic acid 432 Am- ount of Solvent Reaction acid Am- conditions in Com- ount Temp- Pres- Product pro- Ex- pound added erature sure Time Com- Structural Yield duct amples name (g) (° C.) (kPa) (hr) pound formula (%) wt % Ex- ample 33 o- di- chloro ben- zene 100 110 10  6 E-33 [00162] 75 0.03 Ex- ample 34 tol- uene 200 100 80 10 E-34 [00163] 80 0.04 Ex- ample 35 tol- uene 200 100 80 10 E-35 [00164] 82 0.05 Ex- ample 36 tol- uene 200 100 80 10 E-36 [00165] 78 0.06 Ex- ample 37 tol- uene 200 100 80 10 E-37 [00166] 79 0.05

TABLE-US-00007 TABLE 7 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Am- Am- ount ount Acid add- Mole- add- Mole- Com- Ex- Com- Structural ed cular Com- Structural ed cular molar pound amples pound formula (g) weight pound formula (g) weight ratio name Ex- ample 38 A-21 [00167] 200 386 B-18 [00168] 75 493 3.40 p- tol- uene sul- fonic acid Ex- ample 39 A-22 [00169] 200 195 B-9 [00170] 41  75 1.87 phos- phoric acid Ex- ample 40 A-22 [00171] 200 195 B-10 [00172] 48  89 1.9  phos- phoric acid Ex- ample 41 A-22 [00173] 200 195 B-11 [00174] 35 330 9.66 phos- phoric acid Ex- ample 42 A-22 [00175] 200 195 B-12 [00176] 50 479 9.82 phos- phoric acid Ex- ample 43 A-22 [00177] 200 195 B-13 [00178] 75 493 6.74 phos- phoric acid Ex- ample 44 A-22 [00179] 200 195 B-14 [00180] 41 175 4.37 phos- phoric acid Am- ount of Acid Solvent Reaction acid Am- Am- conditions in ount Com- ount Temp- Pres- Product pro- added pound added erature sure Time Com- Structural Yield duct Examples (g) name (g) (° C.) (kPa) (hr) pound formula (%) wt % Example 38 432 toluene 200 100 80 10 E-38 [00181] 77 0.04 Example 39 139 xylene 200 130 40  5 E-39 [00182] 81 0.06 Example 40 139 xylene 200 130 40  5 E-40 [00183] 80 0.04 Example 41 139 xylene 200 130 40  5 E-41 [00184] 81 0.06 Example 42 139 xylene 200 130 40  5 E-42 [00185] 80 0.06 Example 43 139 xylene 200 130 40  5 E-43 [00186] 78 0.07 Example 44 139 xylene 200 130 40  5 E-44 [00187] 81 0.06

TABLE-US-00008 TABLE 8 Raw material 1: Raw material 2: Compound (I) or Compound (III) Compound (IV-I) to (IV-IV) Acid Am- Am- Am- ount Mole- ount Mole- Com- ount Com- Structural added cular Com- Structural added cular molar pound added Examples pound formula (g) weight pound formula (g) weight ratio name (g) Example 45 A-22 [00188] 200 195 B-15 [00189]  48 189 4.03 phos- phoric acid 139 Example 46 A-22 [00190] 200 195 B-16 [00191]  35 290 8.49 phos- phoric acid 139 Example 47 A-22 [00192] 200 195 B-17 [00193]  50 419 8.59 phos- phoric acid 139 Example 48 A-22 [00194] 200 195 B-18 [00195]  75 433 5.92 phos- phoric acid 139 Comparative Example 1 A-7 [00196] 200 182 B-1 [00197]  70  61 0.96 hydrogen chloride 130 Comparative Example 2 A-8 [00198] 150 223 B-5 [00199] 120 181 1.01 hydrogen chloride 277 Am- ount Solvent Reaction of acid Am- conditions in Com- ount Temp- Pres- Product pro- pound added erature sure Time Com- Structural Yield duct Examples name (g) (° C.) (kPa) (hr) pound formula (%) wt % Example 45 xylene 200 130 40 5 E-45 [00200] 79 0.07 Example 46 xylene 200 130 40 5 E-46 [00201] 77 0.04 Example 47 xylene 200 130 40 5 E-47 [00202] 77 0.03 Example 48 xylene 200 130 40 5 E-48 [00203] 78 0.06 Comparative Example 1 toluene 200 100 80 8 E-9 [00204] 55 0.01 Comparative Example 2 toluene 200 100 80 8 E-10 [00205] 50 0.01 [00206]

[0244] As is evident from Examples 1 to 48, the yield of every products was at least 67%, with the target product able to be obtained in high yield. Further, the acid was in a liquid state during the production process, and was not contained in the distilled gaseous component.

INDUSTRIAL APPLICABILITY

[0245] The production method of an embodiment of the present invention can produce an amino acid aminoalkyl ester or an inorganic acid salt thereof in high yield without acid distillation.