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Title:
PREPARATION OF (2R,5R)-3-OXO-7-OXO-1-AZABICYCLO (3. 2. 0 HEPTANE-2-CARBOXYLIC ACIDS)
Document Type and Number:
Japanese Patent JPS5728090
Kind Code:
A
Abstract:

NEW MATERIAL:A (2R,5R)-3-oxo-7-oxo-1-azabicyclo[3. 2. 0]heptane-2-carboxylic acid shown by the formula I (R is H, protecting group, or salt-forming cation).

EXAMPLE: Diphenylmethyl-(2R,5R)-3,7-dioxo-1-azabicyclo[3. 2. 0]heptane-2-carboxylate.

USE: An intermediate for synthesizing carbapenems. An inhibitor for β-lactamase.

PROCESS: R2 or a novel compound shown by the formula II (R1 and R2 are protecting groups) is removed in the presence of an oxidizing agent (e.g., DDQ) to give a compound shown by the formula III, which is subjected to ring closure in the presence of a catalyst (e.g., rhodium acetate), and , if necessary, R1 is removed, or chlorine or a protecting group is introduced after the removal of R1, to give a compound shown by the formula I. The novel compound shown by the formula II is obtained by removing one or both of the protecting groups R3 and R4 of a compound shown by the formula IV, followed by decarboxylation, to give a compound shown by the formula V, which is diazotized.


Inventors:
KOGA KENJI
IKODA NOBUO
SHIBATA HISANARI
Application Number:
JP10187080A
Publication Date:
February 15, 1982
Filing Date:
July 26, 1980
Export Citation:
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Assignee:
TOYAMA CHEMICAL CO LTD
International Classes:
C07D477/00; A61K31/397; A61K31/40; A61P31/04; C07D487/04; (IPC1-7): A61K31/40; C07D487/04