Tetrahedron: Asymmetry

Facile conversion of racemic ibuprofen to (S)-ibuprofen

D Chavez-Flores, JM Salvador

Index: Chavez-Flores, David; Salvador, James M. Tetrahedron Asymmetry, 2012 , vol. 23, # 3-4 p. 237 - 239

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Citation Number: 9

Abstract

The methyl ester of ibuprofen was quantitatively formed by Fischer esterification and converted into (S)-ibuprofen in 94% yield with an ee of 94% under dynamic kinetic resolution conditions at pH 9.8, using Candida rugosa lipase, and 20% DMSO. The (R)- methyl ibuprofen ester was observed to racemize by chiral HPLC without the Candida rugosa lipase present. The rates of in situ racemization and enzymatic hydrolysis for the ...