Hydrofluoric Acid → HCID 69257389, compound

Participants

Reaction Steps

5-Bromo-2-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}phenyl acetate (140.0 mg, 0.223 mmol) was dissolved in acetonitrile (8.0 mL) and 48% hydrofluoric acid (0.8 mL) into a polypropylene Falcon® tube. The reaction was stirred for 4 h at room temperature and then poured into 0.5 M potassium phosphate (50 mL), extracted with 1:1 ethyl acetate-hexane (50 mL), washed with saturated sodium bicarbonate solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, concentrated and purified by chromatography (12 g silica gel, 15% to 90% ethyl acetate-hexane) to afford 5-bromo-2-{(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-1-phenylazetidin-2-yl}phenyl acetate (114.5 mg, 100% yield) as a clear foam; Rf 0.11 (1:4 ethyl acetate-hexane).

Provenance & Evidence