Glycine → HCID 19063687, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(2,4-dioxo-6H-benzo[d][1,3]oxazin-1-yl)-N-isopropyl-N-phenylacetamide (10 g, 31 mmol), glycine (2.32 g, 31 mmol) and triethylamine (4.32 mL, 31 mmol) in water (50 mL) is stirred at 50° C. for 5 h. The reaction mixture is concentrated to a brown viscous oil, acetic acid (100 mL) is added and the mixture heated at reflux for 6 h. The reaction mixture is concentrated to a brown viscous oil, dissolved in ethyl acetate (300 mL) and washed with water, saturated aqueous sodium bicarbonate and brine. The resulting solution is dried over magnesium sulfate and concentrated to a yellow foam. Recrystallization from ethyl acetate/petroleum ether (4:1, 100 mL) gave the title compound (7.55 g, 21.5 mmol) as an off-white powder. 1H NMR (300M Hz, CDCl3): 1.12 (d, J=6.7 Hz, 6H); 3.6-6.4 (m, 4H); 5.05 (m, J=6.7 Hz, 1H); 6.62 (m, 1H); 7.1-7.6 (m, 7H); 7.84 (d, J=7.5 Hz, 1H). MS (FAB): [M+H]+ =352.

Provenance & Evidence