Ethanol → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

(R)-4-methyl-4-(6-(4-(trifluoromethyl)cyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one (0.1442 g, 0.0003665 mol) was dissolved in ethanol (1.00 mL, 0.0171 mol) in a capped vial equipped with a magnetic stir bar. 4.2 M Lithium hydroxide, monohydrate in water (1.00 mL) was added and the mixture was heated overnight at 80° C. with stirring. TLC analysis showed that the reaction was complete. The mixture was concentrated to dryness under vacuum. Water (3 mL) and methylene chloride (3 mL) were added and the layers were separated (2×). The combined organic layers were concentrated under vacuum and purified by HPLC to give the title compound as a TFA salt in 0.0388 g (29% yield). MS: m/z=351.41 [M-NH2]+. 1H NMR (400 MHz, MeOD) δ 1.48-1.65 (m, 2 H), 1.75-1.80 (m, 4 H), 2.04-2.11 (m, 2 H), 2.17-2.25 (m, 2 H), 2.33 (d, J=11.04 Hz, 2 H), 3.79-3.85 (m, 1 H), 3.90-3.95 (m, 1 H), 4.41-4.83 (m, 1 H, 2:1 ratio), 7.16-7.27 (m, 1 H, 2:1 ratio) 7.29-7.32 (m, 1 H), 7.52 (dd, J=8.66, 2.13 Hz, 1 H), 7.79-7.88 (m, 3 H)

Provenance & Evidence