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Title:
PRODUCTION OF HALOMETHYLCARBAPENEM COMPOUND
Document Type and Number:
Japanese Patent JPH04164091
Kind Code:
A
Abstract:

PURPOSE: To obtain the subject compound useful as a synthetic intermediate for antimicrobial agents by reacting a hydroxymethylcarbapenem compound with a phosphorylating agent and then reacting the resultant product with a halogenating agent.

CONSTITUTION: A 2-hydroxymethylcarbapenem compound expressed by formula I [R1 and R2 are H or (substituted) alkyl; R5 is H or carboxy-protecting group] is reacted with a phosphorylating agent in the presence of an acid capturing agent (e.g. dimethylaminopyridine), preferably at -60 to -20°C for 30min to 3hr to provide a 2-phosphoryloxymethylcarbapenem compound expressed by formula II [R3 and R4 are halogen, (substituted) alkoxy or aryloxy], which is subsequently reacted with a halogenating agent (e.g. an alkali metallic halide), preferably at -40°C to ambient temperature for 30min to 3hr to afford the objective 2-halomethylcarbapenem compound expressed by formula III (Hal is halogen).


Inventors:
Ageo, Shoichiro
Imuda, Mitsuru
Ona, Toshio
Itani, Hikari
Application Number:
JP1990000293019
Publication Date:
June 09, 1992
Filing Date:
October 29, 1990
Export Citation:
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Assignee:
SHIONOGI & CO LTD
International Classes:
C07D477/00; A61K31/397; A61K31/40; A61P31/04; C07F9/6561; (IPC1-7): A61K31/40; C07D477/00; C07F9/6561