Hydrochloric Acid → HCID 11180513, compound

Participants

Reaction Steps

A solution of N-[4′-(2-butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid ethyl ester (120 mg, 0.204 mmol) in ethanol (3 mL) was treated with aq 1 N NaOH (0.3 mL, 1.5 equiv., 0.306 mmol) and stirred at room temperature. After stirring 1 h, the solution was acidified to pH<4 with 10% HCl, concentrated and purified by prep thin layer chromatography (10% methanol in dichloromethane) afforded N-[4′-(2-Butyl-benzofuran-3-ylmethyl)-4-(3-phenyl-propoxy)-biphenyl-3-yl]-oxalamic acid (32 mg, 28%). Rf 0.39 (10% methanol in dichloromethane), 1H NMR (DMSO-d6, 300 MHz) δ 10.26 (s, 1H), 8.58 (d, J=2.1 Hz, 1H), 7.43-7.05 (m, 16H), 4.07 (t, J=6.0 Hz, 2H), 3.95 (s, 2H), 2.82-2.77 (m, 4H), 2.13-1.97 (m, 2H), 1.67-1.59 (m, 2H), 1.37-1.24 (m, 2H), 0.86 (t, J=7.5 Hz, 3H).

Provenance & Evidence