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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 33, Number 5
JKCSEZ 33(5)
October 20, 1989 

 
Title
Synthetic Studies on Penems and Carbapenems (Ⅶ). Compounds Derived by Cleavage of the β-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 β-lactam 고리가 절단되어 생성된 화합물들
Author
Han Cheol Wang, Youn Young Lee, Yang Mo Goo, Kyoo-hyun Chung

왕한철, 이윤영, 구양모, 정규현
Keywords
Abstract
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 β-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.

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 β-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).

Page
545 - 550
Full Text
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