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Practical synthetic approach to 4-acetoxy-2-azetidinone for the preparation of carbapenem and penem antibiotics

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Abstract

A practical synthesis of 4-acetoxy-2-azetidinone useful for the preparation of carbapenem- and penem-type antibiotics is described. The synthesis has advantages such as avoiding the tedious and costly column chromatographic or recrystallized separation steps for diastereomers. The overall yield of the product is greatly improved and the process is also more economical for large-scale production. In addition, the mechanism for oxidative decarboxylation is also present.

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Authors and Affiliations

  1. Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou, 310027, China

    Guo-Bin Zhou & Li-Rong Yang

  2. Zhejiang Hisoar Pharmaceutical Co., LTD., No.100 Waisha Branch Rd., Jiaojiang Taizhou, Zhejiang, 318000, China

    Guo-Bin Zhou, Yue-Qing Guan, He Tang & Yan-Bin Zhao

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  1. Guo-Bin Zhou
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  2. Yue-Qing Guan
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  3. He Tang
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  5. Li-Rong Yang
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Correspondence to Guo-Bin Zhou or Li-Rong Yang.

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Zhou, GB., Guan, YQ., Tang, H. et al. Practical synthetic approach to 4-acetoxy-2-azetidinone for the preparation of carbapenem and penem antibiotics. Res Chem Intermed 38, 251–259 (2012). https://doi.org/10.1007/s11164-011-0344-5

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