Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Synthesis of 6-(Carboxymethylthio) penicillanic Acid Derivatives from 6${\beta}$-Bromopenicillanates

6${\beta}$-Bromopenicillanate로부터 6-(Carboxymethylthio) penicillanic Acid 유도체의 합성

  • Won-Sik Choi (Department of Genetic Engineering, Soon Chun Hyang University) ;
  • Young-Haeng Lee (Department of Chemistry, Won Kwang University) ;
  • Chai-Ho Lee (Department of Chemistry, Won Kwang University)
  • Published : 1991.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Reaction of 6${\beta}$-bromopenicillanic acid(4a) with p-nitrobenzylbromide, 3-bromophthalide, chloromethylpivalate and 1-chlorodiethylcarbonate afforded 6${\beta}$-bromopenicillanates(4b~4e). New ${\beta}$-lactam compound, 6-(carboxymethylthio)penicillanic acid(5a) and the other esters(5b~5e) were prepared by nucleophilic substitution reaction of 6${\beta}$-bromopenicillanic acid(4a) and the other esters(4b~4e) with thioglycolic acid.

6${\beta}$-bromopenicillanic acid(4a)와 p-nitrobenzylbromide, 3-bromophthalide, chloromethylpivalate 및 1-chlorodiethylcarbonate의 반응으로 6${\beta}$-bromopenicillanates(4b~4e)을 합성하였으며, 6${\beta}$-bromopenicillanic acid(4a)와 그의 ester(4b~4e)를 thioglycolic acid와 친핵성 치환반응시켜 새로운 $\beta$-lactam계 화합물인 6-(carboxymethylthio)penicillanic acid(5a)와 그의 ester(5b~5e)를 얻었다.

Keywords

References

  1. Recent Advance 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. Org. Chem. v.47 R. A. Volkmann;R. D. Carrol;R. B. Drolt
  4. J. Org. Chem. v.43 M. J. Loosemore;R. F. Pratt
  5. Tetrahedron Lett. J. A. Aimetti;E. S. Hamanaka;D. A. Johson;M. S. Kellogg
  6. Biochem. J. v.177 V. Knott-Hunziker;B. S. Orlek
  7. J. C. S. Chem. Comm. B. S. Orlek;P. G. Sammes
  8. J. Org. Chem. v.55 E. G. Mata;E. L. Setti;O. A. Mascaretti
  9. J. Chem. Soc., Perkin Trans. I E. L. Setti;O. A. Mascaretti
  10. Tetrahedron Lett. v.30 E. G. Mata;O. A. Mascaretti
  11. J. Org. Chem. v.43 J. C. Sheehan;E. Chacko;Y. S. Lo;D. R. Ponzi;E. Sato
  12. Tetrahedron Lett. M. M. Campbell;R. G. Harcus;S. J. Ray
  13. J. Chem. Soc. Chem. Commun. S. A. Matlin;L. Chan
  14. J. Org. Chem. v.42 J. C. Sheehan;J. C. Thomas;Y. S. Lo
  15. J. Chem. Soc., Perkin Trans. I J. G. Peter;D. I. John;J. T. Eric
  16. J. Chem. Soc. Perkin Trans. I B. S. Orlek;P. G. Sammes
  17. J. Chem. Soc. (c) I. Mcmillan;R. J. Stoodley