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Title:
CARBAPENEM INTERMEDIATE
Document Type and Number:
Japanese Patent JPH0827168
Kind Code:
A
Abstract:

PURPOSE: To provide a new compound useful as a synthetic intermediate for carbapenem antibiotic substances such as thienamycin.

CONSTITUTION: This compound is expressed by formula I (R1 to R3 are each a 1-4C alkyl) such as p-nitrobenzyl 2-diazo-3-t-butyldimethylsilyoxy-3-butenoate. The compound can be produced by reacting a p-nitrobenzyl diazoacetoacetate intermediate of formula II with a triorganosilyl triflate silylation agent of formula III (preferably t-butyldimethylsilyl trifluoromethylsufonate) in an inert organic solvent such as THF in the presence of an organic base (preferably a 1-4C trialkylamine) preferably at 0-5°C. The intermediate of the formula II is produced e.g. by reacting ethyl acetoacetate with p-nitrobenzyl alcohol in toluene and reacting the resultant p-nitrobenzyl acetoacetate with a toluene sulfonylazide in the presence of triethylamine.


Inventors:
YASUTSUGU UEDA
GAI ROOBAAGU
Application Number:
JP35545791A
Publication Date:
January 30, 1996
Filing Date:
November 28, 1991
Export Citation:
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Assignee:
BRISTOL MYERS SQUIBB CO
International Classes:
B01J27/135; B01J27/138; C07B61/00; C07C205/42; C07C245/18; C07D205/08; C07D477/00; C07F7/18; (IPC1-7): C07F7/18; B01J27/138
Domestic Patent References:
JPS58103358A1983-06-20
Attorney, Agent or Firm:
Takehiko Saito



 
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