Resolving Ketoprofen Using n-Octyl-d-glucamine as an Optical Resolution Agent

作     者：朱圣东 吴元欣 喻子牛 Zhu Shengdong;WU Yuanxin;Yu Ziniu

作者机构：School of Chemical Engineering and Pharmacy Wuhan Institute of Chemical Technology College of Life Science and Technology Huazhong Agricultural University 

出 版 物：《Chinese Journal of Chemical Engineering》 (中国化学工程学报（英文版）)

年 卷 期：2005年第13卷第4期

页      面：568-571页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

主　　题：ketoprofen resolution n-octyl-d-glucamine 

摘      要：The process of resolution of racemic ketoprofen using n-octyl-d-glucamine as an optical resolution agent was investigated. The process consists of preparation of the diastereomer salt of ketoprofen with n-octyl-d-glucamine, liberation of S-(+)-ketoprofen from its diastereomer salt and recovery of the remaining ketoprofen and n-octyl-d- glucamine. The suitable conditions for preparation of the diastereomer salt were methanol and ethyl acetate (1.1 by volume) as the solvent, the ratio of solvent volume to ketoprofen mass at 8ml:1g, and the molar ratio of ketoprofen to n-octyl-d-glucamine at 1:1. The preferred approach to liberate S-(+)-ketoprofen from its diastereomer salt was alkali dissolution, acid adjustment and ethyl acetate extraction. Racemization of the recovered ketoprofen could be achieved by reacting the recovered ketoprofen with 10% NaOH at 507 kPa for 6h. The recovered n-octyl-d- glucamine could be refined by acid dissolution and alkali adjustment. S-(+)-ketoprofen can be obtained with high optical purity and yield, showing that the present process is a practical and efficient one which can be used in industrial scale for preparation of S-(+)-ketoprofen.