The purpose of the present invention is to provide an industrially preferred method for producing a p-toluenesulfonate of 7-(2,3-difluoro-4-(2-((2-methoxyethyl)(methyl)amino)ethoxy)benzyl)-10-hydroxy-6-methyl-N-(4-methyl-2-(6-methylpyrimidin-4-yl)phenyl)-8-oxo-6,7-diazaspiro[4,5]dec-9-ene-9-carboxamide, which enables a target product to be obtained more inexpensively and easily as compared to conventional methods.

The present invention has attained a method which enables a target product to be efficiently obtained by a step of preparing wet powder of a p-toluenesulfonate of 7-(2,3-difluoro-4-(2-((2-methoxyethyl)(methyl)amino)ethoxy)benzyl)-10-hydroxy-6-methyl-N-(4-methyl-2-(6-methylpyrimidin-4-yl)phenyl)-8-oxo-6,7- diazaspiro[4,5]dec-9-ene-9-carboxamide, and a step of drying the wet powder.

The invention relates to a process for transvinylation of a carboxylic acid feedstock with a vinyl ester feedstock to obtain a vinyl ester product and the corresponding acid of the vinyl ester feedstock in the presence of one or more ruthenium catalysts, wherein a) the vinyl ester feedstock, the carboxylic acid feedstock and a ruthenium catalyst are fed to the reactor, and b) the transvinylation reaction is carried out, characterized in that a carbonyl-free Ru(III) carboxylate is used as the ruthenium catalyst and in that no carbon monoxide is supplied, c) the reaction is carried out at a temperature of 110 to 170 C., d) upon completion of the transvinylation reaction, the vinyl ester feedstock and the corresponding acid are separated from the reaction mixture by distillation, e) the vinyl ester product is separated by distillation from the bottom product of the distillation, and f) the remaining reaction mixture is recycled into the reactor.

Methods and compositions for producing 1-butanol are described herein. In some examples, the methods can comprise, contacting a reactant comprising ethanol with a catalyst system, thereby producing a product comprising 1-butanol. The catalyst system can comprise, for example, an iridium catalyst and a nickel, copper, and/or zinc catalyst. The nickel, copper, and zinc catalysts can comprise nickel, copper, and/or zinc and a sterically bulky ligand.

There are provided a compound capable of being a novel ligand allowing regioselective borylation to be performed in the aromatic borylation reaction, and a catalyst using the same compound. There is provided a bipyridyl compound represented by a general formula (1): (wherein A represents a single bond, a vinylene group or an ethynylene group;

X represents an oxygen atom or a sulfur atom;

n pieces of R.sup.1 may be the same or different, and R.sup.1 represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted amino group, a cyano group, a nitro group, or an alkoxycarbonyl group, or two adjacent R.sup.1 may form a saturated or unsaturated ring structure optionally containing a hetero atom together with the carbon atoms bonded to the two R.sup.1;

R.sup.2 represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group; and

n represents a number of 1 to 4).

##STR00001##

The disclosed embodiments detail improved methods for the synthesis of diketopiperazines from amino acids. In particular improved methods for the cyclocondensation and purification of N-protected 3,6-(aminoalkyl)-2,5-diketopiperazines from N-protected amino acids. Disclosed embodiments describe methods for the synthesis of 3,6-bis-[N-protected aminoalkyl]-2,5-diketopiperazine comprising heating a mixture of an amino acid in the presence of a catalyst in an organic solvent. The catalyst is selected from the group comprising sulfuric acid, phosphoric acid, p-toluenesulfonic acid, 1-propylphosphonic acid cyclic anhydride, tributyl phosphate, phenyl phosphonic acid and phosphorous pentoxide among others. The solvent is selected from the group comprising: dimethylacetamide, N-methyl-2-pyrrolidone, diglyme, ethyl glyme, proglyme, ethyldiglyme, m-cresol, p-cresol, o-cresol, xylenes, ethylene glycol and phenol among others.

A method for preparing formamide compounds via hydrogenation of carbon dioxide catalyzed by porous materials includes the following steps: by taking porous organometallic polymers as catalysts, reacting amine compounds with carbon dioxide and hydrogen under an air atmosphere to prepare formamide compounds. The method has the advantages of high reaction efficiency, good selectivity, mild conditions, economy, environmental protection, and simple operation. The catalysts are solid organometallic polymers with large specific surface area, strong carbon dioxide adsorption, hierarchical pore distribution, and uniformly dispersed metal centers. They are designed and synthesized as the reaction catalysts by changing the proportion of the cross-linked comonomer. The catalysts can be especially used for catalytic synthesis of fine chemical N, N-dimethylformamide (DMF) without addition of any additional solvent, alkali, or other additives, which is convenient for separation and purification of DMF.

The disclosed embodiments detail improved methods for the synthesis of diketopiperazines from amino acids. In particular improved methods for the cyclocondensation and purification of N-protected 3,6-(aminoalkyl)-2,5-diketopiperazines from N-protected amino acids. Disclosed embodiments describe methods for the synthesis of 3,6-bis-[N-protected aminoalkyl]-2,5-diketopiperazine comprising heating a mixture of an amino acid in the presence of a catalyst in an organic solvent. The catalyst is selected from the group comprising sulfuric acid, phosphoric acid, p-toluenesulfonic acid, 1-propylphosphonic acid cyclic anhydride, tributyl phosphate, phenyl phosphonic acid and phosphorous pentoxide among others. The solvent is selected from the group comprising: dimethylacetamide, N-methyl-2-pyrrolidone, diglyme, ethyl glyme, proglyme, ethyldiglyme, m-cresol, p-cresol, o-cresol, xylenes, ethylene glycol and phenol among others.

Disclosed are processes for preparing 5-bromo-3,4-dimethylpyridin-2-amine and 6-bromo-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine: (I), (VI).

##STR00001##

The disclosed embodiments detail improved methods for the synthesis of diketopiperazines from amino acids. In particular improved methods for the cyclocondensation and purification of N-protected 3,6-(aminoalkyl)-2,5-diketopiperazines from N-protected amino acids. Disclosed embodiments describe methods for the synthesis of 3,6-bis-[N-protected aminoalkyl]-2,5-diketopiperazine comprising heating a mixture of an amino acid in the presence of a catalyst in an organic solvent. The catalyst is selected from the group comprising sulfuric acid, phosphoric acid, p-toluenesulfonic acid, 1-propylphosphonic acid cyclic anhydride, tributyl phosphate, phenyl phosphonic acid and phosphorous pentoxide among others. The solvent is selected from the group comprising: dimethylacetamide, N-methyl-2-pyrrolidone, diglyme, ethyl glyme, proglyme, ethyldiglyme, m-cresol, p-cresol, o-cresol, xylenes, ethylene glycol and phenol among others.

A catalyst for depolymerizing a polycarbonate-based resin, the catalyst including a compound represented by Chemical Formula 1:

##STR00001##

where R.sub.1 and R.sub.2 are a straight chain alkyl having 1 to 3 carbon atoms, a preparation method thereof, and a decomposition method of a polycarbonate-based resin, and a recovery method of a catalyst for depolymerizing a polycarbonate-based resin.