New process of producing alpha-hydroxy compounds from sustainable resources useful as platform chemicals, such as hydroxy analogues of amino acids or polymer precursors.

New process of producing alpha-hydroxy compounds from sustainable resources useful as platform chemicals, such as hydroxy analogues of amino acids or polymer precursors.

Process for producing aminocarboxylic acid of formula (I): NH.sub.3CH.sub.2(CH.sub.2).sub.nCOOH (I) including: (i) reacting the unsaturated carboxylic acid of formula (II): CHCH(CH.sub.2).sub.n-1COOH (II) with hydrogen bromide to form the -bromoalkanoic acid of formula (iii): BrCH.sub.2(CH.sub.2).sub.nCOOH (III); (ii) reacting the w-bromoalkanoic acid obtained with ammonia in aqueous solution to form a reaction mixture; (iii) separating the reaction mixture of the aminocarboxylic acid of formula (I) and an aqueous solution rich in ammonium bromide; (iv) bringing the aqueous solution rich in ammonium bromide into contact with sodium hydroxide to form ammonia and an aqueous solution rich in sodium bromide; (v) purifying the aqueous solution rich in sodium bromide; (vi) bringing the purified aqueous solution rich in sodium bromide into contact with chlorine to form bromine and an aqueous solution rich in sodium chloride; (vii) reacting the bromine with hydrogen to form hydrogen bromide; and (viii) recycling the hydrogen bromide to step (i).

Process for producing aminocarboxylic acid of formula (I): NH.sub.3CH.sub.2(CH.sub.2).sub.nCOOH (I) including: (i) reacting the unsaturated carboxylic acid of formula (II): CHCH(CH.sub.2).sub.n-1COOH (II) with hydrogen bromide to form the -bromoalkanoic acid of formula (iii): BrCH.sub.2(CH.sub.2).sub.nCOOH (III); (ii) reacting the w-bromoalkanoic acid obtained with ammonia in aqueous solution to form a reaction mixture; (iii) separating the reaction mixture of the aminocarboxylic acid of formula (I) and an aqueous solution rich in ammonium bromide; (iv) bringing the aqueous solution rich in ammonium bromide into contact with sodium hydroxide to form ammonia and an aqueous solution rich in sodium bromide; (v) purifying the aqueous solution rich in sodium bromide; (vi) bringing the purified aqueous solution rich in sodium bromide into contact with chlorine to form bromine and an aqueous solution rich in sodium chloride; (vii) reacting the bromine with hydrogen to form hydrogen bromide; and (viii) recycling the hydrogen bromide to step (i).

Process for producing aminocarboxylic acid of formula (I): NH.sub.3CH.sub.2(CH.sub.2).sub.nCOOH (I) including: (i) reacting the unsaturated carboxylic acid of formula (II): CHCH(CH.sub.2).sub.n-1COOH (II) with hydrogen bromide to form the -bromoalkanoic acid of formula (iii): BrCH.sub.2(CH.sub.2).sub.nCOOH (III); (ii) reacting the w-bromoalkanoic acid obtained with ammonia in aqueous solution to form a reaction mixture; (iii) separating the reaction mixture of the aminocarboxylic acid of formula (I) and an aqueous solution rich in ammonium bromide; (iv) bringing the aqueous solution rich in ammonium bromide into contact with sodium hydroxide to form ammonia and an aqueous solution rich in sodium bromide; (v) purifying the aqueous solution rich in sodium bromide; (vi) bringing the purified aqueous solution rich in sodium bromide into contact with chlorine to form bromine and an aqueous solution rich in sodium chloride; (vii) reacting the bromine with hydrogen to form hydrogen bromide; and (viii) recycling the hydrogen bromide to step (i).

A compound that includes a menthol glycinate. The menthol glycinate includes a menthol connected to a glycine or glycine derivative, via an ester linkage. The groups on the N atom are referred to as R.sub.1 and R.sub.2, and R.sub.1 and R.sub.2 are independently selected from the group consisting of: alkyl and R.sub.1 and R.sub.2 together with the N atom to which they are attached form a 4-8-member ring. R.sub.1 and R.sub.2 each contain at most 20 carbon atoms.

A compound that includes a menthol glycinate. The menthol glycinate includes a menthol connected to a glycine or glycine derivative, via an ester linkage. The groups on the N atom are referred to as R.sub.1 and R.sub.2, and R.sub.1 and R.sub.2 are independently selected from the group consisting of: alkyl and R.sub.1 and R.sub.2 together with the N atom to which they are attached form a 4-8-member ring. R.sub.1 and R.sub.2 each contain at most 20 carbon atoms.

A method for preparing a lisinopril intermediate is provided. The method includes: treating (R)-hydroxy-4-phenylbutyrate with sulfonyl chloride in an organic solvent in the presence of a base to obtain a solution of sulfonate; reacting the obtained solution with a salt of trifluoroacetyl lysine; and obtaining a N.sup.2-[1-(S)-alkoxycarbonyl-3-phenylpropyl]-N.sup.6-trifluoroacetyl-L-lysine by separating after the reaction is completed. The method provided has a shorter synthesis route, is easy to operate, has a low cost, and is suitable for industrial production.

A method for preparing a lisinopril intermediate is provided. The method includes: treating (R)-hydroxy-4-phenylbutyrate with sulfonyl chloride in an organic solvent in the presence of a base to obtain a solution of sulfonate; reacting the obtained solution with a salt of trifluoroacetyl lysine; and obtaining a N.sup.2-[1-(S)-alkoxycarbonyl-3-phenylpropyl]-N.sup.6-trifluoroacetyl-L-lysine by separating after the reaction is completed. The method provided has a shorter synthesis route, is easy to operate, has a low cost, and is suitable for industrial production.

A method for preparing a lisinopril intermediate is provided. The method includes: treating (R)-hydroxy-4-phenylbutyrate with sulfonyl chloride in an organic solvent in the presence of a base to obtain a solution of sulfonate; reacting the obtained solution with a salt of trifluoroacetyl lysine; and obtaining a N.sup.2-[1-(S)-alkoxycarbonyl-3-phenylpropyl]-N.sup.6-trifluoroacetyl-L-lysine by separating after the reaction is completed. The method provided has a shorter synthesis route, is easy to operate, has a low cost, and is suitable for industrial production.