Process for the enzymatic resolution of N-(alkoxycarbonyl)-4-ket

Details Process for the enzymatic resolution of N-(alkoxycarbonyl)-4-ket Process for the enzymatic resolution of N-(alkoxycarbonyl)-4-ket

1998-06-26

1999-07-27

Saucier, Sandra E.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435107, 435921, C07C 104, C12P 1324

Patent

active

059289333

ABSTRACT:
The present invention relates to a process for the enzymatic resolution of racemic mixtures of N-(alkoxycarbonyl)-4-keto-D,L-proline alkyl esters, using Candida antarctica lipase fraction B (CALB) as enzyme catalyst to enantioselectively hydrolyze the alkyl ester of one of the two enantiomers present. Separating the unreacted N-(alkoxycarbonyl)-4-keto-D-proline alkyl ester from the N-(alkoxycarbonyl)-4-keto-L-proline, followed by hydrogenation of the keto group of the D-isomer and subsequent hydrolysis of the ester and N-(alkoxy-carbonyl) groups produces cis-4-hydroxy-D-proline in high yield. Diastereomeric mixtures of N-(alkoxycarbonyl)-4-hydroxyproline alkyl esters can also be resolved using CALB to ultimately produce cis-4-hydroxy-D-proline or trans-4-hydroxy-L-proline.

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