Acetic Acid → HCID 86596173, compound

Participants

Reaction Steps

To a solution of 4-nitrobenzyl (5R,6S)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-3-{3-[(trimethylsilyl)oxy]phenyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (500 mg) in THF (8.6 ml) was added at −78° C. acetic acid (51 mg). Thereto was dropped 1M tetrabutylammonium fluoride/THF solution (0.86 ml), and the mixture was stirred at the same temperature for 15 minutes. The reaction mixture was poured into a mixture of a cold aqueous sodium hydrogencarbonate (72 mg) and ethyl acetate. The mixture was extracted and separated by a separating funnel. The organic layer was washed with a cold saturated aqueous sodium chloride solution (three times) and cold water in the order, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-nitrobenzyl (5R,6S)-3-(3-hydroxyphenyl)-7-oxo-6-{(1R)-1-[(trimethylsilyl)oxy]ethyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate. This product was used in the next step without further purification.

Provenance & Evidence