Lipase-catalyzed dynamic resolution of naproxen 2,2,2-trifluoroethyl thioester by hydrolysis in isooctane

✍ Scribed by Chun-Sheng Chang; Shau-Wei Tsai; Jimmy Kuo

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 124 KB
• Volume: 64
• Category: Article
• ISSN: 0006-3592
• DOI: 10.1002/(sici)1097-0290(19990705)64:1<120::aid-bit13>3.0.co;2-a

✦ Synopsis

A lipase-catalyzed enantioselective hydrolysis process under continuous in situ racemization of substrate by using trioctylamine as an organic base was developed for the production of (S)-naproxen from racemic naproxen thioesters in isooctane. Naproxen 2,2,2trifluoroethyl thioester and 45°C were selected as the best substrate and temperature, respectively, by comparing the time-course variations for the racemization of (S)naproxen thioesters containing an electron-withdrawing group. A detailed investigation of the effect of trioctylamine concentration on the kinetic behaviors of the thioester in racemization and enzymatic reaction was conducted, in which more than 70% conversion of the racemate (or 67.2% yield of (S)-naproxen) with ee p value higher than 92% was obtained.