Dynamic kinetic resolution of suprofen thioester via coupled trioctylamineand lipase catalysis

A lipase-catalyzed enantioselective hydrolysis process under conditions of continuous in situ racemization of substrate with trioctylamine as the cata lyst was developed for the production of (S)-suprofen from (R,S)-suprofen 2 ,2,2-trifluoroethyl thioester in isooctane. A detailed investigation of tri octylamine concentration on the enzyme activation and stability as well as the kinetic behaviors of the thioester in racemization and enzymatic reacti on was conducted, in which good agreement between the experimental data and theoretical results was observed. A complete conversion of the racemate fo r the desired (S)-suprofen in 95% ee(P) was obtained. Moreover, the recover y of the acid product by extraction and reuse of the organic solution were reported. (C) 2000 John Wiley & Sons, Inc.