Research on Chemical Intermediates

, Volume 39, Issue 8, pp 3911–3917

A scalable chemoenzymatic process for 7-amino-3-[Z-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (ATCA)

Authors

  • Chun Hui Gao
    • School of Chemical EngineeringHebei University of Science and Technology
  • Cheng Guo Jia
    • Department of R&DBrant Pharmaceuticals Co., Ltd.
  • Wei Li
    • Department of R&DBrant Pharmaceuticals Co., Ltd.
    • School of Chemical EngineeringHebei University of Science and Technology
  • Yi Feng Yu
    • School of Chemical EngineeringHebei University of Science and Technology
Article

DOI: 10.1007/s11164-012-0907-0

Cite this article as:
Gao, C.H., Jia, C.G., Li, W. et al. Res Chem Intermed (2013) 39: 3911. doi:10.1007/s11164-012-0907-0

Abstract

An efficient chemoenzymatic process has been developed for preparation of 7-amino-3-[Z-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid, featuring removal of para-methoxybenzyl by trichloroacetic acid and cleavage of phenylacetyl E-isomer by immobilized penicillin acylase enzyme. The E-isomer of 7-amino-3-[Z-2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid could be easily decreased to less than 0.2 % by salt formation. Importantly, trichloroacetic acid and immobilized penicillin acylase enzyme could be recovered and reused. The enzyme reaction could be run in a flow reactor. Only two crystallizations are involved as the purification procedure in the six-step sequence.

Keywords

Cefditoren pivoxil ATCA Deprotection Trichloroacetic acid Immobilized penicillin acylase Process

Copyright information

© Springer Science+Business Media Dordrecht 2012