Acetic Acid → HCID 11606400, compound

Participants

Reaction Conditions

Reaction Steps

Dess-Martin reagent [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1)-one] (174 mg, 0.411 mmol) was added to a solution of the trifluoroacetate salt of N-{(3R,6S)-6-(2,3-difluorophenyl)-2-[(2-hydroxy-3-methylbutyl)imino]azepan-3-yl}-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide (164 mg, 0.206 mmol) and acetic acid (24 μL, 0.411 mmol) in dichloromethane (10 mL). After 1 h, sodium sulfite (100 mg, 0.793 mmol) and ethanol (10 mL) were added and the mixture was heated to 80° C. After 1 h, the reaction was allowed to cool to ambient temperature and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography [100% dichloromethane→93% dichloromethane/methanol)] gave the title compound (76 mg). MS 550.2748 (M+1).

Provenance & Evidence