Reacción #640573

Ecuación de reacción

water

3-[2-(Trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-one

sodium hydrogen carbonate

propyl chloroformate

→

3-{2-[N-(propoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinan-2-one

Rendimiento 68.2%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for six hours
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with a saturated brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Otrothe solvent was evaporated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Procedimiento

3-[2-(Trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazinan-2-one (0.13 g, 0.38 mmol) and sodium hydrogen carbonate (0.06 g, 0.71 mmol) was suspended in acetonitrile (15 ml), added with propyl chloroformate (0.09 g, 0.77 mmol) and heated to reflux for six hours. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 3-{2-[N-(propoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-[1,3]-oxazinan-2-one (0.11 g).

Fuente