反应详情

To a solution of tert-butyl methyl{[4-phenyl-5-(phenylthio)-1,3-thiazol-2-yl]methyl}carbamate (0.27 g) in N,N-dimethylformamide (3 mL) was added 3-chloroperbenzoic acid (0.57 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetic acid (2 mL), 3-chloroperbenzoic acid (0.96 g) was added thereto, and the mixture was stirred at room temperature for 30 min. Aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1) to give the title compound as a pale-yellow oil (yield 0.18 g, 63%).

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in acetic acid (2 mL)
7. addition3-chloroperbenzoic acid (0.96 g) was added
8. stirringthe mixture was stirred at room temperature for 30 min
9. additionAqueous sodium thiosulfate solution was added to the reaction mixture
10. extractionthe mixture was extracted with ethyl acetate
11. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
12. dry with materialdried over anhydrous magnesium sulfate
13. concentrationconcentrated under reduced pressure
14. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1)