Hydrochloric Acid → HCID 11641220, compound

Participants

Reaction Steps

To 3-{3-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ureido}-benzoic acid ethyl ester (200 mg, 0.40 mmol) in 1:1 tetrahydrofuran:methanol (10 mL) is added 2 N NaOH (5 mL). The reaction mixture is stirred vigorously at room temperature for 3 h. The reaction mixture is diluted with water (30 mL), acidified with 5N hydrochloric acid to pH=4, and extracted with ethyl acetate (3×70 mL). The combined organic extracts are washed with brine, dried over sodium sulfate, and concentrated to dryness. The resulting residue is purified by reverse phase HPLC using a gradient of 90:10 to 20:80 (H2O/0.1% TFA):CH3CN as eluent to give the title compound (24 mg, 12%). LC-MS (m/e): 461 (M−1); 1H NMR (DMSO-d6) δ 12.93 (1H, s), 12.85 (1 H, s), 8.93 (1 H, s), 8.77 (1 H, s), 8.15 (1H, s), 7.82 (1H, s), 7.30-7.60 (7 H, m), 6.75 (1H, d), 5.20 (2 H, s), 2.60 (5 H, m), 1.50 (2 H, m), 0.90 (3 H, t).

Provenance & Evidence