手性氯霉胺拆分扁桃酸对映体的研究  

The Optical Resolution of Mandelic Acid Enantiomers by Chiral Chloramphenicol Amine

作　　者：熊非[1] 刘文广 吴思琴 洪丹凤 谈庆港 XIONG Fei;LIU Wenguang;WUSiqin;HONGDanfeng;TANQinggang(Department of Chemistry,University of Shanghai for Science and Technology,Shanghai 200093,Chin)

机构地区：[1]上海理工大学化学系,上海200093

出　　处：《实验室研究与探索》2018年第7期13-15,共3页Research and Exploration In Laboratory

基　　金：国家自然科学基金项目(51707122);上海理工大学教师教学发展研究重点资助项目(CFTD180092);上海理工大学校级大学生创新创业训练计划项目(XJ2017266)

摘　　要：以抑菌性广谱抗生素氯霉素的工业生产副产物右胺作为手性拆分剂,与化学合成的外消旋扁桃酸对映体进行成盐反应,采用非对映体盐结晶拆分法,用50%的乙醇水溶液对其进行重结晶,过滤溶液中析出"(S)-(+)-扁桃酸·(1S,2S)-2-氨基-1-(4-硝基苯基)丙烷-1,3-二醇"非对映异构体盐晶体。经酸化解离和重结晶提纯,以36%的收率和97%的光学纯度分离得到了(S)-(+)-扁桃酸。通过合理利用工业废弃物,实现了外消旋扁桃酸的绿色拆分,可应用于实验教学、科研和生产实践等领域。An efficient process for the preparation of highly enantiomerically pure S-（＋）-mandelic acid via the diastereomeric crystallization resolution strategy is described in this article. The enantiopure diastereomeric salt S-（＋）-mandelic acido（1S,2S）-2-amino-1-（p-nitrophenyl） propane-1,3-diol was obtained by a salification reaction of racemic mandelic acid with commercially available chiral chloramphenicol amine, a by-product in the industrial production of bacteriostatic broad-spectrum antibiotics chloramphenicol, and subsequent crystallization from 50% ethanol aqueous solution. Finally, acid dissociation of the isolated diastereomeric salts and recrystallization afford the corresponding enantiopure S-（＋）-mandelic acid in 36% isolated yield and 97% enantiomeric excess. This method can be used in area of experiment teaching, scientific research and industrial manufacture which related to the rational use of industrial solid waste.

关 键 词：手性氯霉胺 (1S 2S)-2-氨基-1-(4-硝基苯基)丙烷-1 3-二醇 化学拆分 (S)-(+)-扁桃酸 

分 类 号：O625.54[理学—有机化学]