Lithium Hydroxide → HCID 59599512, compound

Participants

Reaction Steps

Dissolve 3-[5-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-pyridin-3-ylsulfanyl]-benzoic acid methyl ester (379 mg, 0.84 mmol) in methanol (2 mL) and water (0.5 mL). Add 2N aqueous lithium hydroxide solution (0.42 mL, 0.84 mmol). After 12 hours, concentrate under reduced pressure and dissolve residue in 4N hydrochloric acid in dioxane. Add water until white precipitate forms, and collect by filtration. Triturate in ethyl acetate, then methanol. Collect the title compound by filtration as a white solid (317 mg, 0.73 mmol): 1H NMR (DMSO-d6) δ 0.76 (t, 3H), 1.37 (m, 2H), 2.47 (m, 2H), 2.58 (s, 3H), 5.30 (s, 2H), 6.70 (d, 1H), 7.52 (t, 1H), 7.63 (m, 1H), 7.77 (m, 1H), 7.80 (m, 1H), 7.86 (m, 1H), 7.90 (d, 1H), 8.60 (m, 2H), 12.83 (s, 1H), 13.21 (br s, 1H); MS (m/z): 438 (M+1).

Provenance & Evidence