Hydrochloric Acid → 5-[(3-Cyclopentylpropanoyl)(4-{[(4-phenoxybenzyl)amino]carbonyl}-benzyl)amino]-2-hydroxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[(3-cyclopentylpropanoyl)(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}-N-(4-phenoxybenzyl)benzamide (200 mg) in EtOH (3 mL) was added an aqueous solution (0.071 mL, 1N). The mixture was heated at 70° C. for 3 h. After cooling to rt, an aqueous solution of HCl (2 mL, 1N) was added and the resulting reaction mixture was extracted (EtOAc). The combined organic layers were washed with water, brine, dried over MgSO4, filtered and evaporated to give the title compound as a white powder (160 mg, 85%). 1H NMR (DMSO-d) δ 8.99 (t, J=6.0 Hz, 1H), 7.82 (d, J=8.2 Hz, 2H), 7.50 (d, J=2.6 Hz, 1H), 7.42-7.06 (m, 8H), 7.03-6.89 (m, 5H), 4.85 (s, 2H), 4.45 (s, 1H), 4.43 (s, 1H), 3.40 (brs, 1H), 2.05 (t, J=7.5 Hz, 2H), 1.70-1.32 (m, 9H), 1.00-0.81 (m, 2H). M+(ESI): 593.0; M−(ESI): 591.0. HPLC, Rt: 4.9 min purity: 99.3%).

Provenance & Evidence