Triethylamine → HCID 91514082, compound

Participants

Reaction Steps

To a solution of Example 81A (343 mg, 1.3 mmol) and triethylamine (0.9 ml, 6.5 mmol) in ethanol/water (95:5, v/v, 10 mL) was added hydroxylamine hydrochloride (228 mg, 3.25 mmol). The reaction was heated at reflux for 15 minutes and concentrated on a rotary evaporator. The residual solids were dissolved in dichloromethane (50 mL), and washed with water (50 mL) and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 10% to 30% ethyl acetate in hexanes to provide 372 mg of the title compound (96%) as a off-white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.30 (d, J=6.25 Hz, 6H) 5.11-5.33 (m, 1H) 6.03 (s, 2H) 6.84 (d, J=9.19 Hz, 1H) 7.61 (s, 1H) 7.78 (dd, J=9.01, 3.13 Hz, 1H) 8.22 (d, J=2.94 Hz, 1H) 9.71 (s, 1H); MS (ESI) m/z 295.0 (M+H)+.

Provenance & Evidence