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以葡辛胺为拆分剂拆分酮基布洛芬
引用本文:朱圣东,吴元欣,喻子牛. 以葡辛胺为拆分剂拆分酮基布洛芬[J]. 中国化学工程学报, 2005, 13(4): 568-571
作者姓名:朱圣东  吴元欣  喻子牛
作者单位:[1]School of Chemical Engineering and Pharmacy, Wuhan Institute of Chemical Technology, Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, Wuhan 430073, China [2]College of Life Science and Technology, Huazhong Agricultural University, Wuhan 430070, China
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 8 ml:1 g, 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 507kPa 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.

关 键 词:酮基布洛芬 葡辛胺 拆分剂 拆分工艺 手性药物
收稿时间:2004-11-10
修稿时间:2004-11-102005-04-22

Resolving Ketoprofen Using n-Octyl-d-glucamine as an Optical Resolution Agent
ZHU,nbsp,Shengdong,XU,nbsp,Yuanxin,YU,nbsp,Ziniu. Resolving Ketoprofen Using n-Octyl-d-glucamine as an Optical Resolution Agent[J]. Chinese Journal of Chemical Engineering, 2005, 13(4): 568-571
Authors:ZHU   Shengdong  XU   Yuanxin  YU   Ziniu
Affiliation:School of Chemical Engineering and Pharmacy, Wuhan Institute of Chemical Technology, Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, Wuhan 430073, China;College of Life Science and Technology, Huazhong Agricultural University, Wuhan 430070, China
Abstract: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-dglucamine. 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 8 ml:1 g, 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 6 h. The recovered n-octyl-dglucamine 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.
Keywords:ketoprofen  resolution  n-octyl-d-glucamine
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