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

  1. Jenkinson, S. G.; Briggs, M. S.; Bryn, R. D. J. Antimicrob. Chemother. 1980, 6, 177. https://doi.org/10.1093/jac/6.suppl_A.177
  2. Neu, H. C. Ann. Intern. Med. 1982, 97,408. https://doi.org/10.7326/0003-4819-97-3-408
  3. Fujimoto, K.; Ishihara, S.; Yanagisawa, H.; Ide, J.; Nakayama, E.;Nakao, H.; Sugawara, S.; Iwata, M. J. Antibiot. 1987, 40, 370. https://doi.org/10.7164/antibiotics.40.370
  4. Hitzel, V.; Latrell, D. Chem. Abs. 1979, 92: p22513w.
  5. Ro-Rodriguez,J. C.; Hernandez, R.; Gonzalez, M.; López, M. A.; Fini,A. Farmaco 2000, 55, 393. https://doi.org/10.1016/S0014-827X(00)00058-6
  6. Rodriguez, J. C.; Hernandez, R.;Gonalez, Z.; Rodriguez, Z.; Tolon, B.; Velez, H.; Valdes, B.;López, M. A.; Fini, A. Farmaco 2003, 58, 363. https://doi.org/10.1016/S0014-827X(03)00051-X
  7. Udayampalayam, P. S.; Sivakumaran, S.; Sahoo, P. K. PCT WO 2008041100, 2008 CAN 148:426634
  8. Lim, S. K.; Moon, S. K.; Lee, G. S. EP 175814, 1986; CAN 105:114832.
  9. Koh, D.; Kim, J. H.; Park, S. W.; Kim, Y. Bull. Korean Chem. Soc. 1987, 8, 418.
  10. Ohki, H.; Kawbata, K.; Inamoto, Y.;Okuda, S.; Kamimura, T.; Sakane, K. Bioorg. Med. Chem. 1997,5, 1685. https://doi.org/10.1016/S0968-0896(97)00092-8
  11. An, S.-H.; Lee, K.-H.; Yun, M.-S.; Kim, Y.-J.; Jang, M.-S. KR 951357, 1995; CAN 133:177061.
  12. Lee, H.-W.; Kang, T. W.; Cha, K. H.; Kim, E.-N.; Choi, N. -H.;Kim, J.-W.; Hong, C. I. Synth. Commun. 1998, 28, 35. https://doi.org/10.1080/00397919808005071
  13. Kang,T.-W.; Moon, W.-S.; Choi, Y.-W.; Hwang, K.-J. PCT WO 1996012712, 1996; CAN 125:114388.
  14. Takeuchi, Y: Yamada,S. Chem. Pharm. Bull. 1974, 22, 832. https://doi.org/10.1248/cpb.22.832
  15. Zenoni, M.; Leone, M.; Sala, B. IT 1301988, 2000; CAN 137: 154929.
  16. Lee, C.-S.; Ryu, E.-J.; Oh, S. H.; Paek, K.-S.; Kim,M. Y.; Youn, H. Bioorg. Med. Chem. Lett. 2000, 10, 2123. https://doi.org/10.1016/S0960-894X(00)00425-X

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