Ethyl Acetate → HCID 58844408, compound

Participants

Reaction Steps

A solution of sodium (5R,6S)-3-(4-{[(aminocarbonyl)oxy]methyl}phenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (13 mg) in dry dimethylformamide (0.5 ml) was cooled with ice, and thereto were added N,N-diisopropylethylamine (5 mg), benzyltriethylammonium chloride (5 mg) and pivaloyloxymethyl chloride (11 mg). The mixture was gradually warmed to room temperature and stirred for overnight. To the reaction mixture were added ethyl acetate and ice water to separate by a separating funnel. The organic layer was washed with cold water (three times) and a cold saturated aqueous sodium chloride solution (twice), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel thin-layer chromatography (ethyl acetate) to give [(2,2-dimethylpropanoyl)oxy]methyl (5R,6S)-3-(4-{[(aminocarbonyl)oxy]methyl}phenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (9.2 mg).

Provenance & Evidence