Ethyl Acetate → HCID 9844859, compound

Participants

Reaction Steps

Sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.17 g) was dissolved in dry DMF (1.7 ml) and the solution was ice-cooled. Thereto was gradually dropped pivaloyloxymethyl iodide (0.12 g) in dry DMF (1.2 ml) and the mixture was stirred. Thirty minutes later, ethyl acetate was added thereto and the mixture was washed with bicarbonate solution, water and brine, successively. The organic layer was dried over sodium sulfate, concentrated and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2˜ethyl acetate only) to give [(2,2-dimethylpropanoyl)oxymethyl(5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(4-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.15 g, yield 70%).

Provenance & Evidence