Process for the production of antibiotic penems
    5.
    发明授权
    Process for the production of antibiotic penems 失效
    生产抗生素penems的过程

    公开(公告)号:US4443373A

    公开(公告)日:1984-04-17

    申请号:US363710

    申请日:1982-03-30

    摘要: There is disclosed a process for preparing 6-hydroxyethyl-2-alkylthio penem-3-carboxylates by a multi-step process comprising reacting an azetidinone having a protected hydroxy group at the 5 position with a diester of ketomalonic acid, chlorinating the resulting N-substituted azetidinone, removing the chlorine and OH protecting group, reacting the resulting compound with a silver salt to form a silver thio substituted at the 4 position of the azetidinone, cyclizing with a thiocarbonyl compound, then reacting the resulting penam with a fluoride to form a penam-penem tautomer, reacting the tautomer with a halide or ethylenically unsaturated compound followed by deprotecting the carboxyl at the 3 position to form the final penem product in high yield.

    摘要翻译: 公开了通过多步法制备6-羟乙基-2-烷硫基半胱胺-3-羧酸盐的方法,包括使5位具有被保护的羟基的氮杂环丁酮与酮缩醇酸的二酯反应,氯化得到的N- 取代的氮杂环丁酮,除去氯和OH保护基团,使所得化合物与银盐反应,形成在氮杂环丁酮的4位被取代的硫代硫酸酯,用硫代羰基化合物环化,然后使所得的penam与氟化物反应形成 双氯吡啶互变异构体,使互变异构体与卤化物或烯属不饱和化合物反应,然后在3位上脱羧保护羧基,以高产率形成最终的penem产物。