3-(S)-巯基-1-(N-对硝基苄氧羰基乙酰亚胺)四氢吡咯的合成

Synthesis of 3-(S)-(+)-3-mercapto-1-(N-p-nitrobenzyloxy-carbonyl acetimidoyl)pyrrolidine

对标题化合物的合成工艺作了改进。以L-羟基脯氨酸为原料,环己酮作催化剂,经脱羧获得的3-(R)-羟基四氢吡咯盐酸盐,与由乙醇和乙腈反应得到的乙氧基乙酰亚胺盐酸盐,经5步反应成功地合成了目标产物,总收率为15.6%,关键中间体及目标化合物经过1HNMR检测,还探讨了标题化合物及其前体的构型转化问题。

To synthesize 3-（ S）=（ ＋ ）-3-mercapto-1-（ N-p-nitrobenzyloxycarbonyl aeetimidoyl） pyrrolidine, the＇ ：main intermediates of Carbapenem BS-533 and its isomers rind to improve the synthetic procedure, starting from L-hydroxypraline, in the presence of cyclohexanone as catalyst,3-（ R）-（-）-3-hydroxypyrrolidine hydrochlofide was prepared.Ethoxyacetimidate hydrochloride was prepared in high yield with alcohol and acetonitrile. Solid potassium thiolacetate was used to produce the target compound after five-step reaction, instead of sodium hydride and thiol-acetic acid. The key intermediates were analysized by ^1HNMR. The conversions of configuration of the product and its intermediate were discussed in the article. The overall yield was 15.6%. This preparation method could be used industrially.