Hydrochloric Acid → 4-{[(3-cyclopentylpropanoyl)(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}-N-(4-phenoxybenzyl)benzamide

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}benzoic acid (212 mg) in THF (2 mL) was added NMM (57 mg). The mixture was chilled at 0° C. and isobutyl chloroformate was added at once (86 mg). The mixture was stirred for 15 min. at 0° C. then 4-phenoxybenzylamine (103 mg) was added and the resulting reaction mixture was stirred 3 h at rt. An aqueous solution oh HCl (1N, 2 mL) was added and the resulting mixture was extracted with Et2O. The combined organic layers were washed with water, brine, dried over MgSO4 filtered and evaporated to give a light yellow oil. Purification by chromatography (SiO2) gave the title compound as a colorless oil (241 mg, 81%). 1H NMR (CDCl3) δ 7.56-7.42 (m, 3H), 7.21-7.00 (m, 6H), 6.95-6.67 (m, 7H), 6.21 (t, J=4.9 Hz, 1H), 4.69 (s, 2H), 4.42 (s, 1H), 4.40 (s, 1H), 1.87 (t, J=7.2 Hz, 2H), 1.54 (s, 6H), 1.48-1.14 (m, 9H), 0.85-0.64 (m, 2M). M+(ESI): 633.0; M−(ESI): 631.0. HPLC, Rt: 5.3 min (purity: 97.7%).

Provenance & Evidence