(2S,5R)-N-[(Z)-N-hydroxy-C-methylcarbonimidoyl]-7-oxo-6-phenylmethoxy-1,6-diazabicyclo[3.2.1]octane-2-carboxamide → (2S,5R)-6-(benzyloxy)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one

Participants

Reaction Steps

A solution of (2S,5R)-6-(benzyloxy)-N—((Z)-1-(hydroxyimino)ethyl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (174 mg, 0.524 mmol) in DMF (2 mL) was heated at 80° C. for 2-3 hrs. The solvent was then concentrated in vacuum and the residue was purified by silica gel column chromatography (0 to 5% MeOH/DCM) to provide (2S,5R)-6-(benzyloxy)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (130 mg, 79%) as a white solid.

Provenance & Evidence