超临界流体萃取拆分手性外消旋伪麻黄碱  

RESOLUTION OF DL-PSEUDOEPHEDRINE BY SUPERCRITICAL FLUID EXTRACTION

作　　者：高丽红[1] 赵平[2] 蔡水洪[2] 柴逸峰[1] 刘荔荔[1] 吴玉田[1] 

机构地区：[1]第二军医大学药学院,上海200433 [2]华东理工大学化工学院,上海200237

出　　处：《药学学报》2002年第12期959-962,共4页Acta Pharmaceutica Sinica

基　　金：国家自然科学基金资助项目 ( 39770 90 4)

摘　　要：目的　用超临界CO2 流体萃取技术拆分伪麻黄碱异构体。方法　用单通路法 ,毛细管电泳分析。将消旋伪麻黄碱转化为非对映体盐 ,用超临界二氧化碳作为萃取溶剂 ,可从反应混合物中选择性萃取出伪麻黄碱的一个异构体 ,达到拆分伪麻黄碱的目的。结果　酒石酸是伪麻黄碱良好的拆分剂 ,半摩尔法形成非对映体盐以超临界二氧化碳流体萃取拆分 ,一次萃取产物e .e .值可达 10 0 %。结论　对拆分剂及非对映体盐进行分子构键的计算结果表明拆分剂与被拆分物质成盐的反应规律为R构型优先与S构型反应 ,理论预测与拆分结果基本吻合。AIM To establish a method for resolution of dl-pseudoephedrine by supercritical fluid extraction and to investigate the influence of some parameters upon the resolution process. METHODS Using single-pass method and HPCE method for determination. RESULTS As it was demonstrated by the resolution of the racemic pseudoephedrine, CO 2 density and resolving agent can influence the extraction process. Tartaric acid is a good resolving agent, it was shown that a high degree of resolution (100% e.e.) can be achieved within a single extraction step. Dibenzoyl-L-tartaric acid which was ramifications of tartaric acid, showed remarkable partial resolutions, while other resolving agents such as malic acid, phenylalanine, camphorsulfonic acid showed poor partial resolutions at the same condition. In standard experiments, racemic pseudoephedrine was allowed to react with 0.5 equivaient of the chiral agents. Extraction at 0.25, 0.50, 0.75 and 1.0 molar ratios of (2S,3S)-(-)-tartaric acid and dl-pseudoephedrine showed that increase of the molar ratio did not enhance the enantiomeric excess. CONCLUSION Calculation of molecular force showed that R-acid prefers to react with S-pseudoephedrine. It was comported with experimental results.

关 键 词：超临界流体萃取 伪麻黄碱 拆分 超临界CO2流体萃取技术 麻黄碱异物体 单通路法 毛细管电泳分析 

分 类 号：R917[医药卫生—药物分析学]