Réaction #48416

Équation de réaction

sodium carbonate

Sodium periodate

tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-1-[2-(methylthio)ethyl]-2-oxoazepan-3-ylcarbamate

sodium periodate

→

title compound

tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-1-[2-(methylsulfinyl)ethyl]-2-oxoazepan-3-ylcarbamate

Solvants

methanol

water

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   LavageThe organic layer was washed with saturated aqueous sodium carbonate (3×), saturated brine
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Mode opératoire

Sodium periodate (11.3 mg, 0.053 mmol) was added to a solution of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-1-[2-(methylthio)ethyl]-2-oxoazepan-3-ylcarbamate (22 mg, 0.053 mmol) in methanol (2 mL) and water (2 mL). After 30 min excess sodium periodate (22 mg, 0.11 mmol) was added. After 18 h, saturated aqueous sodium carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. MS 431 (M+1).

Source