Lithium Hydroxide → HCID 11532424, compound

Participants

Reaction Steps

Add 1N lithium hydroxide (30 mL) to a solution of 3-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoylamino]-benzoic acid methyl ester (4.00 g, 8.67 mmol) in tetrahydrofuran (40 mL). Stir overnight at room temperature and then dilute with water. Acidify the resulting mixture (the salt precipitated) with 1N hydrochloric acid. Concentrate to remove the organic solvents, filter and wash with water several times, then with hexanes. Dry to afford the title compound as a white powder (3.56 g, 92%): 1H NMR (DMSO-d6) δ 0.83 (t, 3H), 1.50 (sextet, 2H), 2.58 (s, 3H), 2.62 (t, 2H), 5.36 (s, 2H), 6.75 (d, 1H), 7.49 (t, 1H), 7.59 (t, 1H), 7.67 (d, 1H), 7.71 (d, 1H), 7.82 (d, 1H), 7.96 (d, 1H), 8.04 (d, 1H), 8.06 (s, 1H), 8.41 (s, 1H), 10.49 (s, 1H), 12.85 (s, 1H), 13.00 (bs, 1H); MS (APCI-neg mode) m/z (rel intensity) 446 (100).

Provenance & Evidence