Reaction #640579

Reaction equation

water

6-Methyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazepan-2-one

sodium hydrogen carbonate

isobutyl chloroformate

→

3-(2-[N-(isobutoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-6-methyl-[1,3]-oxazepan-2-one

Yield 52.3%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for three hours
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe ethyl acetate layer was washed with a saturated brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Otherthe solvent was evaporated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Procedure

6-Methyl-3-[2-(trifluoromethanesulfonylamino)benzyl]-[1,3]-oxazepan-2-one (0.15 g, 0.41 mmol) and sodium hydrogen carbonate (0.06 g, 0.71 mmol) were suspended in acetonitrile (10 ml), added with isobutyl chloroformate (00.10 g, 0.73 mmol) and heated to reflux for three hours. After cooling to room temperature, the reaction mixture was added with water and extracted with ethyl acetate. The ethyl acetate 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=3:1) to obtain 3-(2-[N-(isobutoxycarbonyl)-N-(trifluoromethanesulfonyl)amino]benzyl)-6-methyl-[1,3]-oxazepan-2-one (0.10 g).

Source