Hydrochloric Acid → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzoic acid

Participants

Reaction Conditions

Reaction Steps

Add 1M aqueous lithium hydroxide (3.23 mL, 3.23 mmol) to a solution of 3-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzoic acid methyl ester (280 mg, 0.646 mmol) in isopropanol (25 mL) and stir. Heat to 80° C. After 1 hour, pour reaction into 1N aqueous hydrochloric acid (50 mL) and extract with ethyl acetate. Combine organic layers, dry with sodium sulfate, filter and concentrate to dryness. Purify the resulting residue by trituration (ether:hexanes) to yield the title compound as a yellow solid (200 mg, 74%): 1H NMR (DMSO-d6) δ 0.81 (t, 3H), 1.46 (sextuplet, 2H), 2.58 (m, 5H), 5.23 (s, 2H), 6.71 (d, 1H), 6.94 (d, 1H), 7.02 (d, 1H), 7.19 (s, 1H), 7.29 (m, 3H), 7.40 (d, 1H), 7.65 (s, 1H), 7.81 (d, 1H), 8.44 (s, 1H), 12.73-12.92 (bs, 1H), 12.84 (s, 1H); MS (esi negative) m/z (rel intensity) 418 (100).

Provenance & Evidence