(S)-1-(N-烯丙氧羰基)亚胺乙基-3-巯基吡咯烷的合成

目的 合成帕尼培南关键中间体 (S)-1-( N-烯丙氧羰基)亚胺乙基-3-巯基吡咯烷。方法 以氯甲酸烯丙酯为酰化剂，与盐酸乙脒进行 N-酰化反应得到 1-亚胺乙基氨基甲酸烯丙酯，该化合物与 3-R-羟基吡咯烷进行缩合，再经甲磺酰化、S_N2 取代、水解共 5 步反应得到目标化合物。结果与结论 该合成路线中使用新型保护基烯丙氧羰基替代传统的保护基—对硝基苄氧羰基，目标化合物的结构经 ¹H-NMR、MS 谱确证，总收率为 41.6%，各步反应操作简便，条件温和，有利于工业化生产。

Synthesis of (S)-1-[N-(allyloxycarbonyl)acetimidoyl]-3-mercaptopyrrolidine

(S)-1-N-(allyloxycarbonyl)acetimidoyl]-3-mercaptopyrrolidine (1) was the key intermediate of panipenem, which was a kind of carbapenem antibiotic. In the traditional method of synthesizing panipenem, the protecting group was removed by catalytic hydrogenation, and the product was purified by macroporous resin. In this synthetic process, allyloxycarbonyl as a new protection group was used instead of p-nitrobenzyloxycarbonyl to synthesize compound 1. The target compound was synthesized from allyl chloroformate and acetamidine hydrochloride through 5 steps, N-acylation, condensation, sulfonylation, substitution reaction and hydrolysis. The chemical structure was confirmed by MS and ¹H-NMR. The overall yield was 41.6%. This new route was provided with mild condition, easy operation and suitable for industrialized production.