Water → Benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]oct-3-ene-2-carboxylate (3.0 g.) in tetrahydrofuran (22 ml.) was added alminum amalgam at 4° C., which was prepared by alminium power (1.8 g.) and 0.5% mercuric chloride (4 ml.), and water (0.75 ml.) was added dropwise thereto. After the mixture was stirred at 10° C. for 75 minutes under nitrogen atmosphere, the reaction mixture was diluted with ethyl acetate (50 ml.) and filtered through a pad of Celite. The filter cake was washed with ethyl acetate, and the filtrate and washings were combined, washed twice with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to leave an oil (2.7 g.). Chromatography on silica gel (15 g.) with a mixed solvent of methylene chloride and ethyl acetate (5:1 by volume) as an eluent gave an amorphous solid (2.64 g.) of benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate.

Provenance & Evidence