A Study on the Synthesis of New Medicinal Agents : Synthesis of 6-Thiocyanopenicillanic Acid Derivatives

새로운 의약품의 합성에 관한 연구 : 6-Thiocyanopenicillanic Acid 유도체의 합성

  • Lee Young-Haeng (Department of Chemistry, Won Kwang University) ;
  • Lee Chai-Ho (Department of Chemistry, Won Kwang University) ;
  • Choi Won-Sik (Department of Genetic Engineering, Soon Chun Hyang University)
  • Published : 1992.10.20

Abstract

A new ${\beta}$-lactam compound, 6-thiocyanopenicillanic acid(1a) was prepared by the reaction of diazonium salt of 6-aminopenicillanic acid with sodium thiocyanate. Reaction of 6-thiocyanopenicillanic acid(1a) with p-nitrobenzyl bromide, chloromethylpivalate and 1-chlorodiethylcarbonate, respectively, afforded the corresponding esters(1b∼d)

6-aminopenicillanic acid의 diazo화 반응과 sodium thiocyanate와 반응으로 새로운 ${\beta}$-lactam 화합물인 6-thiocyanopenicillanic acid(1a)를 합성하고 p-nitrobenzyl bromide, chloromethylpivalate 및 1-chlorodiethylcarbonate들과의 반응에 의해 각각 해당되는 esters(1b∼d)를 합성하였다

Keywords

References

  1. Recent Advanced in the Chemistry of ${\beta}$-Lactam Antibiotics G. I. Gregory
  2. Chemistry and Biology of ${\beta}$-Lactam Antibiotics v.2 R. B. Morin
  3. J. Chem. Soc. Chem. Commun. T. T. Howarth
  4. J. Antibiotic v.29 A. G. Brown
  5. J. Org. Chem. v.47 R. A. Volkmann;R. D. Carrol;R. B. Drolt
  6. J. Org. Chem. v.43 M. J. Loosemore;R. f. Pratt
  7. Tetrahedron Lett. v.48 J. A. Aimetti;E. S. Hamanaka;D. A. Johson;M. S. Kellogg
  8. Biochem. J. v.177 V. Knott-Hunziker;B. S. Orlek
  9. J. C. S. Che, Commun B. S. Orlek;P. G. Sammes
  10. J. Org. Chem. v.55 E. G. Mata;E. L. Setti;O. A. Mascaretti
  11. J. Chem. Soc. Perkin Trans. I E. L. Setti;O. A. Macearetti
  12. J. Kor. Chem. Soc. v.35 W. S. Choi;Y. H. Lee;C. H. Lee
  13. Tetrahedron Lett. v.30 E. G. Mata;O. A. Macearetti
  14. J. Org. Chem. v.43 J. C. Sheehan;E. Chack;Y. S. Lo;D. R. Ponzi;E. Sato
  15. Tetrahedron Lett. M. M. Campbell;R. G. Harcus;S. J. Ray
  16. J. Chem. Soc. Chem. Commun S. A. Matlin;L. Chan
  17. J. Org. Chem. v.42 J. C. Sheehan;J. C. Thomas;Y. S. Lo
  18. J. Chem. Soc. Perkin Trans. I J. G. Peter;D. I. John;J. T. Eric
  19. J. Chem. Soc. Perkin Trans. I B. S. Orlek;P. G. Sammers
  20. J. Chem. Soc. no.C I. Mcmillan;R. J. Stoodley
  21. J. Antibiotics v.44 L. C. Yuhpyang