Water → HCID 131733517, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 16 (0.70 g, 2 mmol) in ethanol (20 mL) was added 4M solution of KOH in H2O (4 mL, 16 mmol) and the mixture was stirred at 90° C. for 12 h. The mixture was concentrated under reduced pressure to get a brown oil material, which was resolved over silica column eluting with CH2Cl2:MeOH (95:5) and then changing to (90:10) to get compound 17 as light brown thick oil (0.51 g, 84%). IR (KBr) vmax. cm−1: 3421, 3411 (NH), 3053 (Ar—H), 2936 (Alph-H), 1697 (C═O), 1606, 1578 (C═C), 1244 (C—N), 1166 (C—O). 1H NMR (500 MHz, CDCl3) δ=1.47 (s, 9H, (C(CH3)3), 3.10 (br. s, 4H, 2CH2), 3.22 (br. s, 4H, 2CH2), 4.08 (s, 2H, CH2), 4.58 (br. s, 2H, NH2), 5.18 (br. s, 2H, NH2), 6.68 (dd, 1H, J=2.3, 9.3 Hz, H-6), 6.73 (br. s, 1H, H-2), 6.81 (d, 1H, J=9.2 Hz, H-5). 13C NMR (125.7 MHz, CDCl3) δ 28.05 (C(CH3)3), 42.43 (CH2), 45.26 (CH2), 50.54 (CH2), 79.75 (C(CH3)3), 112.01 (aromatic-C), 112.08 (aromatic-C), 117.00 (aromatic-C), 130.28 (aromatic-C), 134.08 (aromatic-C), 143.08 (aromatic-C), 154.70 (CO). Calculated (%) for C16H26N4O2 (306.21); C, 62.72; H, 8.55; N, 18.29. found (%); C, 62.66; H, 8.62; N, 18.20.

Provenance & Evidence