Process for producing halomethylcarbapenems

摘要

A functionallized intermediate for antibacterial carbapenems, 2-halomethylcarbapenem (III) is effectively synthesized by treating 2-hydroxymethylcarbapenem (I) with a phosphorylating reagent to give 2-phosphoryloxymethylcarbapenem (II) and then treating this product with a halogenating reagent. Some carbapenems derived from the intermediate are also disclosed. <IMAGE> (I) <IMAGE> (II) <IMAGE> (III) wherein, R1 is hydrogen or substituted or unsubstituted alkyl; R2 is hydrogen or substituted or unsubstituted alkyl; R3, R4 is halogen or substituted or unsubstituted alkoxy or aryloxy; R5 is hydrogen or carboxy protecting group; and Hal is halogen.