SIOC English
化学学报
高级检索

化学学报 ›› 1956, Vol. 22 ›› Issue (1): 24-32. 上一篇    下一篇

论文

制备氯微素的有用中间体的合成及若干有关的缩合

高怡生, 潘百川, 陆顺兴, 徐修容, 陈志豪   

  1. 中国科学院药物研究所, 上海
  • 投稿日期:1955-09-15 发布日期:2013-06-04

SYNTHESIS OF A USEFUL INTERMEDIATE FOR THE PREPARATION OF CHLORAMPHENICOL AND SOME RELATED CONDENSATIONS

KAO YEE-SHENG, PAN PEI-CHUAN, LOH SHUEN-HSING, HSU HSIU-YONG, CHEN CHI-HAO   

  1. Institute of Materia Medica, Academia Sinica
  • Received:1955-09-15 Published:2013-06-04

PDF

378

被引次数

2

1. 本文叙述了从α-苯甲醯-β-乙氧基丙烯酸乙酯开始经过四个步骤合成了制备氯霉素的有用中间体——dl-threo-3-氯代-3-苯基-2-氨基丙醇盐酸盐(Ⅳ)。2. 用 Reformatsky 反应合成了α-甲氧甲基-β-羟基-β-苯基丙酸甲酯(Ⅹ),虽然产量甚小,但说明了β位置含有甲氧基的α溴酯化合物可以应用于Reformatsky反应,而所得的产物为相应的β羟基酸酯而非不饱和酸酯。3. 进行了β羰基醯胺与甲醛的缩合,结果所得者为二分子β羰基醯胺与一分子甲醛缩合成戊二酸醯胺衍生物,而未取得羟甲基化合物。 4. 对硝基苯甲醯乙酸乙酯与过量的甲醛进行缩合,结果获得双羟甲基化合物,αα'-双-羟甲基-对硝基苯甲醯乙酸乙酯(ⅩⅧ)。

The synthesis of dl-threo-3-chloro-3-phenyl-2-aminopropanol hydrochloride (Ⅳ), a useful intermediate for the preparation of racemic chloramphenicol[4], has been achieved by treating 1-phenyl-2-amino-3-ethoxypropanol hydrochloride (Ⅴ), m.p. 119-120°, with concentrated hydrochloric acid in sealed tube; the ethoxy group being converted to hydroxyl, and the replacement of secondary hydroxyl by chlorine having also taken place. The compound Ⅴ was in turn prepared by a 3-step synthesis starting with ethyl α-benzoyl-β-ethoxyacrylate (Ⅵ).