Trifluoromethanesulfonic acid → HCID 58844805, compound

Participants

Reaction Steps

To a solution of allyl (5R,6S)-3-[3-({[(methylamino)carbonyl]oxy}methyl)phenyl]-7-oxo-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (284 mg) in THF (4 ml) was added a solution of anhydrous trifluoromethanesulfonic acid (0.6 ml) in water (2 ml) at 0° C., and the solution was stirred for 25 minutes. Thereto was added a cold aqueous saturated sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to give allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-[3-({[(methylamino)carbonyl]oxy}methyl)phenyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (139 mg).

Provenance & Evidence