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Title:
PRODUCTION OF CARBAPENEM INTERMEDIATE
Document Type and Number:
Japanese Patent JPH09176113
Kind Code:
A
Abstract:

To obtain an intermediate compound containing p-nitrobenzyl ester- protecting group useful for synthesizing thienamycin and other carbapenem antibiotics.

This carbapenem synthetic intermediate is shown by formula I (R4 is H or a hydroxyl-protecting group) such as (3R,4R)-3-{(1R)1[(2,4,6-tri-tert- butylphenoxy)dimethylsilyloxy]ethyl}-4-[3-(4nitrobenzyloxy)carbonyl-2-oxo-3- diazopropyl]azetidin-2-one. The compound of formula I is obtained by reacting a compound of formula II (L is an eliminable group; R4' is a hydroxyl-protecting group) with an enol silyl ether of formula III (R1, R2 and R3 are each irrelevantly a 1-4C alkyl) in the presence of a Lewis acid (e.g. ZnCl2) in an inert organic solvent (e.g. methylene chloride).


Inventors:
YASUTSUGU UEDA
GAI ROOBAAGU
Application Number:
JP22619596A
Publication Date:
July 08, 1997
Filing Date:
August 28, 1996
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): C07D205/08; B01J27/135; C07F7/18
Attorney, Agent or Firm:
Takehiko Saito