Ethanol → HCID 178445754, compound

Participants

Reaction Steps

(R)-4-[6-trans-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (Example 24, 0.03878 g, 0.0001016 mol) was dissolved in Ethanol (1.00 mL, 0.0171 mol) in a capped 40 mL vial equipped with a magnetic stir bar. 4.2 M of lithium hydroxide monohydrate in water (1.00 mL) was added and the reaction was refluxed overnight. TLC analysis showed that the reaction was complete. The solvent was removed under vacuum. The product was diluted in methylene chloride (5 mL) and water was added (5 mL). The layers were separated and the organic phase was then concentrated to dryness under vacuum, and purified by HPLC to give 48 mg of the title compound (13% yield). MS: m/z=339.47 [M−NH2]+. 1H NMR (400 MHz, MeOD) δ 0.92-0.97 (m, 9H), 1.10-1.20 (m, 1H), 1.23-1.35 (m, 2H), 1.39-1.51 (m, 2H), 1.79 (s, 3H), 1.90-1.98 (m, 2H), 2.29 (dd, J=12.55, 2.01 Hz, 2H), 3.81-3.86 (m, 1H), 3.91-3.96 (m, 1H), 4.32-4.43 (m, 1H), 7.19 (dd, J=8.78, 2.51 Hz, 1H), 7.28 (d, J=2.26 Hz, 1H), 7.53 (dd, J=8.66, 2.13 Hz, 1 H), 7.80-7.89 (m, 3H)

Provenance & Evidence