METHOD OF PRODUCING R-BETA-AMINOPHENYL-BUTYRIC ACID DERIVATIVES Russian patent published in 2013 - IPC C07C227/34 C07C227/04 C07C229/34 C07B57/00 

FIELD: chemistry; pharmaceutics.

SUBSTANCE: invention relates to a method of producing R-beta-aminophenyl-butyric acid derivatives of formula (I) where Ar is an unsubstituted phenyl or a phenyl that is substituted with 1-5 substitutes selected from a group consisting of a fluorine atom, methyl, trifluoromethyl and trifluoromethoxy; R¹ is a hydrogen atom or C_1-6 alkyl; and R² is a hydrogen atom or amino-protective group, which includes an alkoxy carbonyl or acyl, which can be used in synthesis of various chiral drugs. The method involves (1) reacting ammonium formate with unsubstituted or substituted phenyl ethyl acetoacetate to obtain an imine, then reacting the imine with a reducing agent to obtain a racemate of beta-aminophenyl-butyric acid ester; (2) reacting the racemate of beta-aminophenyl-butyric acid ester and a resolving agent, which is D-tartaric acids, diacylated with benzoyl or substituted benzyol, to obtain a salt in an alcohol solvent or in an aqueous solution of an alcohol, and crystallising the salt; and (3) hydrolysis of the salt formed from R-beta-aminophenyl-butyric acid ester and the resolving agent, with possible protection of the amino group to obtain R-beta-aminophenyl-butyric acid derivatives of formula (I).

EFFECT: method enables to obtain a compound of formula (I) with high optical purity and high output.

12 cl, 8 ex