Ethanol → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

(R)-4-[6-(trans4-tert-Butylcyclohexyloxy)-5-trifluoromethylnaphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.3341 g, 0.0007433 mol) was dissolved in ethanol (3.00 mL, 0.0514 mol) in a 40 mL capped vial equipped with a magnetic stir bar. 4.2 M Lithium hydroxide, monohydrate in water (3.00 mL) was added and the mixture was heated at 80° C. overnight. HPLC and LCMS analysis showed that the reaction was complete. The solvent was removed under vacuum. Methylene chloride (5 mL) and water (5 mL) were added and the layers were separated. The combined organic layers were concentrated under vacuum and purified by HPLC to give the title compound as a TFA salt in 0.105 g (33% yield). MS: m/z=407.38 [M-NH2]+. 1H NMR (400 MHz, MeOD) δ 0.93 (s, 9 H), 1.10-1.31 (m, 3 H), 1.58 (d, J=12.55 Hz, 2 H), 1.81 (s, 3 H), 1.89-1.98 (m, 2 H), 2.20-2.29 (m, 2 H), 3.82-3.88 (m, 1 H), 3.92-4.00 (m, 1 H), 4.38-4.48 (m, 1 H), 7.40 (d, J=8.78 Hz, 1 H), 7.64 (dd, J=9.04, 2.01 Hz, 1 H), 7.89 (d, J=2.01 Hz, 1 H), 7.93 (d, J=9.04 Hz, 1 H), 8.21 (d, J=9.04 Hz, 1 H)

Provenance & Evidence