Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Development of an Isolable Active Ester, Diethyl Thiophosphoryl [(Z)-(2-Aminothiazol-4-yl)-2-(Methoxyimino)acetate (DAMA) for the Synthesis of Cefotaxime

  • Yoon, Man-Young (Process Research & Development, LG Life Science Ltd., R&D Park) ;
  • Lee, Hee-Bong (Process Research & Development, LG Life Science Ltd., R&D Park) ;
  • Shin, Hyun-Ik (Process Research & Development, LG Life Science Ltd., R&D Park)
  • Received : 2010.10.02
  • Accepted : 2010.11.20
  • Published : 2011.02.20
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Abstract

An isolable activated ester, diethyl thiophosphoryl [(Z)-(2-aminothiazol-4-yl)-2-(methoxyimino)acetate (9a, DAMA) was prepared in high purity, which was at least stable for 7 d at $25^{\circ}C$ and 6 months at $5^{\circ}C$. Its reaction with 7-ACA (4) in the presence of tributylamine in i-PrOH provided cefotaxime (1) of high purity in good yield. Preparation of DAMA and its reaction with 7-ACA (4) to 1 was performed in one-pot manner, respectively with minimal unit operations of stirring and filtration.

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References

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Cited by

  1. ChemInform Abstract: Development of an Isolable Active Ester, Diethyl Thiophosphoryl (Z)-(2-Aminothiazol-4-yl)-2-(methoxyimino)acetate (DAMA) (III) for the Synthesis of Cefotaxime (V). vol.42, pp.28, 2011, https://doi.org/10.1002/chin.201128197