Triethylamine → 6-Methyl-6-phenyl-3-(4-phenylthiazol-2-yl)-1,3-oxazinan-2-one

Participants

Reaction Steps

To a solution of 2-phenyl-4-(4-phenylthiazol-2-ylamino)butan-2-ol (50 mg, 0.15 mmol) and Et3N (80 mg, 0.75 mmol) in CH2CH2 (5 mL) was added triphosgene (15 mg, 0.05 mmol) at 0° C. Then, the mixture was stirred at rt overnight. The reaction solution was concentrated to give an oil, which was purified by column chromatography (1:2 petroleum ether/EtOAc) to afford 6-methyl-6-phenyl-3-(4-phenylthiazol-2-yl)-1,3-oxazinan-2-one (20 mg, 37%). LC-MS Method 3, tR=1.446 min, m/z=351. 1H NMR (CDCl3, 400 Hz): 1.80 (s, 3H), 2.45 (m, 1H), 2.65 b (m, 1H), 3.70 (m, 1H), 4.42 (m, 1H), 7.18 (s, 1H), 7.20-7.40 (m, 8H), 7.80 (d, 2H).

Provenance & Evidence