Ethanol → HCID 178445758, compound

Participants

Reaction Steps

The mixture of (R)-4-(5-trifluoromethyl-6-(cis-4-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (324.6 mg, 0.0007221 mol) and lithium hydroxide (190 mg, 0.0079 mol) in ethanol (10 mL, 0.2 mol) and water (3 mL, 0.1 mol) was heated to reflux for overnight. LCMS showed reaction completed. The solvent was removed under vacuum and the residue was partitioned between water and CH2Cl2. The aqueous layer was extensively extracted with CH2Cl2. And the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into DCM and subjected to chromatographic purification with CH2Cl2/MeOH (10:90 to 80:20) to give the product (303.5 mg, 99% yield). LCMS 407.28 ([M-NH2]+, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.92 (t, J=6.8 Hz, 3H), 1.20-1.69 (m, 13H), 1.51 (s, 3H), 2.05 (dd, J=13.2, 2.3 Hz, 2 H), 3.66 (d, J=10.9 Hz, 1H), 3.73 (d, J=10.9 Hz, 1H), 4.83 (brs, 1H), 7.43 (d, J=9.4 Hz, 1H), 7.68 (dd, J=9.4, 2.3 Hz, 1H), 7.92 (d, J=2.3 Hz, 1H), 8.03 (d, J=9.4 Hz, 1H), 8.12 (dd, J=9.0, 1.8 Hz, 1H).

Provenance & Evidence