反应详情

温度

20 °C

A mixture of alcohol 70 (100 mg, 0.41 mmol), 4-(dimethylamino)butanoic acid hydrochloride (68 mg, 0.41 mmol), DCC (93 mg, 0.45 mmol), DMAP (5 mg, 0.04 mmol) and Et3N (0.06 mL, 0.41 mmol) in DCM (20 mL) was stirred at 20° C. for 16 h. The solvent was evaporated and the residue purified by chromatography, eluting with a gradient (0-10%) of MeOH/20% EtOAc/DCM, to give the ester 309 (137 mg, 94%) as a pale-brown oil: 1H NMR δ 8.25 (s, 1H, H-9), 7.74 (s, 1H, H-5), 4.21 (t, J=6.3 Hz, 2H, CH2O), 3.06-3.15 (m, 6H, H-6, H-8, CH2), 2.73 (br s, 2H, H-7), 2.56 [s, 6H, N(CH3)2], 2.37 (t, J=7.0 Hz, 2H, CH2), 2.18-2.29 (m, 4H, CH2), 1.92-1.99 (m, 2H, CH2); 13C NMR δ 172.6, 164.9, 154.9, 149.1, 147.4, 132.3, 122.7, 114.2, 63.7, 57.7, 43.9 (2), 33.6, 33.2, 32.8, 31.3, 26.8, 25.7, 21.0; HRMS calcd for C19H26N4O3 (M+) m/z 358.2005, found 358.2006.

1. customThe solvent was evaporated
2. customthe residue purified by chromatography
3. washeluting with a gradient (0-10%) of MeOH/20% EtOAc/DCM