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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、SN2取代、水解共5步反应得到目标化合物。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。结果与结论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。
Objective To synthesize the key intermediate of panipenem (S) -1- (N-allyloxycarbonyl) imide ethyl-3-mercaptopyrrolidine. Methods Allyl chloroformate was used as acylating agent to N-acylation with acetamidine hydrochloride to give 1-iminomethyl ethyl carbamate, which was condensed with 3-R-hydroxypyrrolidine and then Mesylation, SN2 substitution, hydrolysis a total of five steps to give the target compound. In this synthetic route, a new protected allyloxycarbonyl group is used instead of the conventional protecting group, p-nitrobenzyloxycarbonyl. Results and Conclusion The structure of the target compound was confirmed by 1H-NMR and MS. The total yield was 41.6%. The reaction was simple and convenient under all conditions. It was favorable for industrial production.