Acetic Acid → allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-trimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate obtained in Example 7-1) in ethyl acetate (73 ml) were added acetic acid (12.5 ml) and a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (51.1 ml) at 0° C. After stirring at 0° C. for 30 minutes, the reaction mixture was taken up into a mixture of ethyl acetate (300 ml) and water (175 ml). The organic layer was separated, washed in turn with water, brine, aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (315 ml) eluting with a mixture of n-hexane and ethyl acetate (9:1-2:5 V/V) to give allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (20.40 g).

Provenance & Evidence