Reaction Steps
To substrate 1-[4-[4-(1-Ethoxycarbonyl-1-methylethoxy)phenyl]butyryl]-2-(3,4-dichlorophenylmethyl)-4-(propyl)semicarbazide (0.4976 g, 0.901 mmol) and camphorsulfonic acid (0.2078 g, 0.895 mmol) was added ethyl acetate (10 mL) and the resulting solution heated to reflux for 12 h. The solution was diluted with ethyl acetate, then washed with sat'd aq. NaHCO3 followed by sat'd aq. NaCl. It was then dried (MgSO4), filtered and concentrated to afford the title compound as an oil (0.4532 g (0.848 mmol, 94%): 1H NMR (DMSO-d6) δ 7.59 (d, 1H, J=8.5 Hz), 7.47 (d, 1H, J=2 Hz), 7.19 (dd, 1H, J=8.5, 2 Hz), 7.03 (d, 2 H, J=8.5 Hz), 6.69 (d, 2H, J=8.5 Hz), 4.85 (s, 2H), 4.13 (q, 2H, J=7 Hz), 3.48 (t, 2H, J=8 Hz), 2.55 (t, 2H, J=7 Hz), 1.83 (m, 2H), 1.52 (q, 2H, J=7 Hz), 1.47 (s, 6H), 1.14 (t, 3H, J=7 Hz), 0.79 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ 174.0, 154.1, 153.8, 147.3, 139.2, 135.6, 131.7, 131.5, 130.8, 130.1, 129.8, 128.4, 119.6, 79.3, 61.6, 47.3, 42.9, 34.0, 27.7, 25.7, 24.7, 22.4, 14.6, 11.5; IR (CHCl3) 3003, 2939, 1728, 1696, 1509 cm−1; HRMS calcd. for C27H34Cl2N3O4 (M+H)+: 524.1926. Found: 534.1935
