Enantioselective enzymatic aminolysis of a racemic 2-isoxazolylacetate alkyl ester

Abstract

Pseudomonas cepacia lipase or Candida antartica lipase B catalyzes the enantioselective aminolysis of a racemic 2-isoxazolylacetate alkyl ester, isobutyl 2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate, by 3-amino-N-(butoxycarbonyl)-L-alanine methyl ester, mono(4-methylbenzenesulfonate) to produce the corresponding amide, (R)-methyl-3-[[[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino]-N-(butoxycarbonyl)-L-alanine, which is an intermediate in the preparation of an isoxazoline-based platelet glycoprotein IIb/IIIa antagonist. Key words: enantioselective aminolysis, Pseudomonas cepacia lipase, Candida antartica lipase B.