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Title:
1-CARBAPENAM-3-CARBOXYLIC ACID DERIVATIVE AND ITS PREPARATION
Document Type and Number:
Japanese Patent JPS5728091
Kind Code:
A
Abstract:

NEW MATERIAL:A compound shown by the formula I (R1 and R2 are lower alkyl, etc.; R3 is H, lower alkyl, etc.; R4 is H or trimethylsilyl; R5 is H, alkali metal, etc.).

EXAMPLE: 1,1-Dimethyl-2-hydroxy-1-carbapenam-3-carboxylic acid benzyl ester.

USE: An intermediate for synthesizing a thienamycin type antibiotic. Also having antibacterial activiey by itself.

PROCESS: 4-(1,1-Substituted-2-propenyl) azetidine-2-one is reacted with an acetic ester, and oxidized to give an aldehyde derivative shown by the formula II. This compound is reacted with a Grignard reagent, to give a compound shown by the formula III, which is subjected to intramolecular aldol reaction in the presence of a base, and, if necessary, the ester part is removed or converted, to give a compound shown by the formula I.


Inventors:
KUBOTA HARUTOSHI
SHIBUYA MASAYUKI
Application Number:
JP10333080A
Publication Date:
February 15, 1982
Filing Date:
July 28, 1980
Export Citation:
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Assignee:
DAIICHI SEIYAKU CO
International Classes:
C07D477/00; A61K31/397; A61K31/40; A61K31/695; A61P31/04; C07D487/04; C07D487/10; C07F7/10; C07F7/18; (IPC1-7): A61K31/40; A61K31/695; C07D487/04; C07D487/10; C07F7/10



 
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