Hydrochloric Acid → HCID 57884475, compound

Participants

Reaction Steps

Add lithium hydroxide (1M aqueous solution, 11.4 mL, 11.4 mmol) to a solution of 5-{[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-nicotinonitrile (473 mg, 1.14 mmol) in dioxane (10 mL). Heat reaction to 80° C. After 2 hours, cool to room temperature and pour into water (50 ml). Wash solution with ethyl acetate (25 mL), and discard. Acidify the aqueous layer with 10% hydrochloric acid, and extract with 25% isopropyl alcohol:75% dichloromethane. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to give a residue. Sonicate the residue in acetonitrile (10 mL), and filter to yield the title compound as a beige solid (210 mg, 42%): 1H NMR (DMSO-d6) δ 0.86 (t, 3H), 1.47 (sextet, 2H), 2.55-2.59 (m, 5H), 5.22 (bs, 2H), 5.90 (bs, 1H), 6.70 (d, 1H), 7.43 (q, 4H), 7.79 (d, 1H), 8.21 (t, 1H), 8.82 (d, 1H), 8.92 (d, 1H), 12.84 (s, 1H); MS (esi negative) m/z (rel intensity) 434 (100).

Provenance & Evidence