Ethanol → HCID 178464725, compound

Participants

Reaction Steps

The mixture of (R)-4-Methyl-4-[6-(cis-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-oxazolidin-2-one (30.6 mg, 0.0000778 mol) and 4.20 M aqueous lithium hydroxide (0.300 mL, 0.00126 mol) and ethanol (0.900 mL, 0.0154 mol) was heated to reflux for 4.5 h. The reaction was evaporated to remove organics. The aqueous phase was extracted with methylene chloride, and the organics were evaporated. The residue was purified by silica gel chromatography using 0-100% methanol in methylene chloride to yield the product in 13.4 mg yield (47%). MS: m/z=351.20 [M−NH2]+. 1H NMR (400 MHz, METHANOL-d4) δ ppm: 7.87 (d, J=2.0 Hz, 1H), 7.80 (d, J=9.0 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.57 (dd, J=8.5, 2.0 Hz, 1H), 7.25 (d, J=2.3 Hz, 1H), 7.18 (dd, J=8.8, 2.5 Hz, 1H), 4.77-4.82 (m, 1H), 3.74 (d, J=10.8 Hz, 1H), 3.70 (d, J=10.8 Hz, 1H), 2.25-2.34 (m, 1H), 2.18-2.25 (m, 2H), 1.65-1.88 (m, 6H), 1.54 (s, 3H).

Provenance & Evidence