反应详情

To a solution of 8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[3-methyl-4-[[[4-methyl-1-propylimidazol-5-yl]methyl]sulfanyl]phenyl]-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxamide (290 mg) in dichloromethane (10 ml) was added dropwise a 70% solution of 3-chloro-perbenzoic acid (111 mg) in dichloromethane (10 ml) at −78° C. After stirring as such for 1 hour, the dry ice-acetone bath was removed, and an aqueous sodium thiosulfate solution was added under vigorous stirring. The mixture was returned to room temperature and stirred for 30 minutes, after which water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine, and was dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was separated and purified with basic silica gel column chromatography (ethyl acetate→methanol:ethyl acetate=1:30) and recrystallized from hexane-ethyl acetate to give 8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[3-methyl-4-[[[4-methyl-1-propylimidazol-5-yl]methyl]sulfinyl]phenyl]-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxamide (232 mg) as yellow crystals (Compound 41).

1. customthe dry ice-acetone bath was removed
2. additionan aqueous sodium thiosulfate solution was added under vigorous stirring
3. customwas returned to room temperature
4. stirringstirred for 30 minutes
5. additionafter which water was added
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine
8. dry with materialwas dried with magnesium sulfate
9. distillationThe solvent was distilled off under reduced pressure
10. customthe resulting residue was separated
11. custompurified with basic silica gel column chromatography (ethyl acetate→methanol:ethyl acetate=1:30)
12. customrecrystallized from hexane-ethyl acetate