Process for the preparation of nateglinide

Details Process for the preparation of nateglinide Process for the preparation of nateglinide

C - Chemistry, Metallurgy

07

C

C07C 231/02 (2006.01) A61K 31/165 (2006.01) A61P 3/10 (2006.01) C07C 233/63 (2006.01)

Patent

CA 2570041

One-pot process for the preparation of nateglinide, which process comprises reacting an alkyl ester of D-phenylalanine of formula (II) where R represents C1-4alkyl, typically methyl, either as the free base or in salt form (typically the hydrochloride), with trans-4-isopropylcyclohexanecarboxylic acid of formula (III) where X represents hydroxy or halo, typically chloro, to obtain a C1-4 alkyl ester of nateglinide of formula (IV), preferably the methyl ester of nateglinide followed by hydrolysis to yield nateglinide of formula (I).

L'invention concerne un procédé monotope de fabrication de natéglinide consistant à faire réagir un alkylester de D-phénylalanine de la formule (II), dans laquelle R est C¿1-4?-alkyl, notamment méthyl, soit sous forme de base libre, soit sous forme de sel (notamment de chlorhydrate), avec de l'acide trans-4-isopropylcyclohexane-carboxylique de la formule (III), dans laquelle X est hydroxy ou halo, notamment chloro, de manière à obtenir un C¿1-4?-alkylester de natéglinide de la formule (IV), de préférence le méthylester de natéglinide, puis à réaliser une hydrolyse de manière à obtenir le natéglinide de la formule (I).

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