PRODUCTION OF HALOMETHYLCARBAPENEM COMPOUND

摘要

PURPOSE:To obtain the subject compound useful as an antibacterial agent by reacting a hydroxymethylcarbapenem compound with a phosphating agent and reacting the product with a halogenation agent. CONSTITUTION:The objective 2-halomethylcarbapenem compound of formula III (Hal is halogen) can be produced by reacting a 2-hydroxymethylcarbapenem compound of formula I [R<1> and R<2> are H or (substituted) alkyl; R<5> is H or carboxy-protecting group] with a phosphating agent in an inert solvent (e.g. dichloromethane) preferably in the presence of an acid acceptor such as dimethylaminopyridine at -40 deg.C for 30min and reacting the resultant 2- phosphoryloxymethylcarbapenem compound of formula II [R<3> and R<4> are halogen, (substituted) alkoxy or aryloxy] with a halogenation agent (e.g. alkali metal or alkaline-earth metal halide).