Process for preparing (2s, 3r)- or (2r, 3s)-3- (alkylphenyl)...

C - Chemistry – Metallurgy – 12 – P

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C12P 41/00 (2006.01) C12P 17/02 (2006.01)

Patent

CA 2074674

The present invention is directed to a process for preparing optically active 3-phenylglycidic acid esters comprising reacting a racemic trans-3-phenyl-glycidic acid with an alkanol in the presence of a hydrolase to esterify preferentially either (2S, 3R) isomer or (2R, 3S) isomer of said racemic compound and isolating and collecting the resulting optically active 3-phenylglycidic acid ester from the reaction mixture, whereby the optically active ester can be produced in a single step and in a highly pure form. The optically active 3-phenylglycidic acid esters are useful for the preparation of 1,5-benzothiazepine derivatives having pharmacological activities such as platelet aggregation inhibitory activity.

La présente invention porte sur une méthode pour préparer des esters d'acide 3-phénylglycidique, consistant à faire réagir un racémique d'acide trans-3-phénylglycidique avec un alcanol en présence d'un hydrolase pour estérifier de préférence soit l'isomère (2S, 3R), soit l'isomère (2R, 3S) de ce composé racémique, et à isoler et recueillir à partir du mélange réactionnel l'ester de l'acide 3-phénylglycidique optiquement actif résultant; cet ester optiquement actif peut être produit en une seule étape et sous une forme très pure. Les esters d'acide 3-phénylglycidique optiquement actifs sont utiles pour la préparation de dérivés de 1,5-benzothiazépine, possédant des propriétés pharmacologiques, notamment une activité inhibitrice de l'agrégation plaquettaire.

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