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Summary
Novelty: An effective synthesis of 2-halomethylcarbapenems (III) and functionalized intermediates for antibacterial carbapenems is disclosed. Additionally, elaboration to some novel carbapenem derivatives is described.
Biology: MIC values against S. aureus Smith, E. coli EC-14 and P. aeruginosa SR-24 for the carbapenems synthesized are documented.
Chemistry: The 2-hydroxymethylcarbapenem is phosphorylated with, for example, diphenylphosphoric acid chloride. The product, on halogenation, gives the halomethylcarbapenem. Four examples of halide displacement followed by deprotection, provide carbapenems such as 1 β-methyl-2-pyridiniomethyl-6α-(1-hydroxy ethyl)-1-carba-2-penem-4-carboxylate.