Methanol--water (1/1) → HCID 57489504, compound

Participants

Reaction Steps

A solution of sodium (meta)periodate (49 mg, 0.23 mmol) in 1:1 methanol/water (6 mL) was cooled with a ice bath and a solution of 1-(3-(4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-3-fluoroazetidin-1-yl)-2-(methylthio)ethanone (102 mg, 0.19 mmol) in methanol (˜2 mL) was added drop wise via pipette. A precipitate forms and the reaction was allowed to stir with the ice bath in place slowly warming to ambient overnight. When complete, the reaction was partitioned between water (5 mL) and CH2Cl2 (5 mL). Aqueous extracted with additional CH2Cl2 (2×5 mL). Organic phase collected and condensed. The crude material was adsorbed on silica and chromatographed on a 12 g silica column, eluting with a gradient of 0% to 100% ethyl acetate in heptane. Fractions containing the desired material were combined and concentrated. CH2Cl2 (˜100 μL) was added to the resulting film. Placing the flask on high vacuum overnight resulted in formation of a white foam. Yield 90 mg (86%). LC/MS retention time=3.317 minutes, MS calculated for (C22H17Cl2F5N2O3S), 554.03; found 555.0 M+H+.

Provenance & Evidence