Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthetic Studies on Penems and Carbapenems (VII). Compounds Derived by Cleavage of the $\beta$-Lactam Ring during (Alkylthio) thiocarbonylation of a 4-Mercapto-3-phenylacetamidoazetidin-2-one Derivative

Penems와 Carbapenems의 합성에 관한 연구 (제 7 보) 4-mercapto-3-phenylacetamidoazetidin-2-one 유도체의 (알킬티오) 티오카르보닐화 과정 중 $\beta$-lactam 고리가 절단되어 생성된 화합물들

  • 왕한철 (서울대학교 자연과학대학 화학과) ;
  • 이윤영 (서울대학교 자연과학대학 화학과) ;
  • 구양모 (서울대학교 약학대학 약학과) ;
  • 정규현 (인하대학교 이과대학 화학과)
  • Published : 1989.10.20
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Abstract

When (3R,4R)-1-(1-benzyloxycarbonyl-2-methyl-1-propenyl)-4-mercapto-3-phenylacetamidoazetidin-2-one(8) was reacted with carbon disulfide and alkyl halides in the presence of triethylamine, the ${\beta}$-lactam ring was cleaved to give (Z)-and (E)-1-alkylthio-5-benzyloxycarbonyl-6-methyl-2-phenylacetamido-4-aza-1,5-heptadien-3-one (13-16) or 2-benzyl-4-(3-benzyloxycarbonyl-4-methyl-1-oxo-2-aza-3-pentenyl)thiazole(17).

트리에틸아민 존재하에서 (3R, 4R)-1-(1-벤질옥시카르보닐-2-메틸-1-메틸-프로펜일)-4-메르캅토-3-페닐아세트아미도아제티딘-2-온(8)에 이황화 탄소화 할로겐화 알킬을 반응시켰을 때 ${\beta}$-락탐 고리가 절단된 (Z)- 및 (E)-1-알킬티오-5-벤질옥시카르보닐-6-메틸-2-페닐아세트아미도-4-아자-1,5-헵타디엔-3-온(13-16) 또는 2-벤질-4-(3-벤질옥시카르보닐-4-메틸-1-옥소-2-아자-3-펜텐일)티아졸(17)이 생성되었다.

Keywords

References

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