泰比培南侧链合成工艺改进

An improved synthesis of the side chain of tebipenem

报道了一种改进的泰比培南侧链合成方法.以苄胺和环氧氯丙烷为起始原料,经取代开环,N-烷基化反应构建四元环分子骨架,该中间体再经氢化、N-叔丁氧羰基化、O-甲烷磺酰化、取代反应、成盐等8步操作合成泰比培南侧链,总收率24.3%.与现有方法相比,反应条件温和,操作简便,试剂廉价易得.

Aiming at improving the synthetic process of the side chain of tebipenem and employing benzylamine and epichlorohydrin as starting materials, a four - membered ring was constructed as the molecular framework via ring - opening substitution and N - alkylation. Subsequently, this intermediate was transformed into the side chain of tebi- penem through 8 synthetic steps, e.g. hydrogenation, N - tert - butoxycarbonylation, O - mesylation, substitution and saltification ; starting from benzylamine, the side chain of tebipenem was prepared via 10 steps with a total yield of 24.3% ; an improved method for the synthesis of the side chain of tebipenem was developed. Compared with the known methods, the new synthetic approach has the advantages of a mild reaction condition, simple operation and cheap chemical reagents, thus showing a promising prospect.