反应详情

To a solution of tert-butyl [(1R,2R,3S)-4-azido-3-cyclopropyl-2-hydroxy-1-(hydroxymethyl)butyl]carbamate (0.435 g, 1.45 mmol) in anhydrous pyridine (5 mL) was added 4-dimethylaminopyridine (0.055 g, 0.20 mmol) and para-toluenesulfonyl chloride (0.55 g, 2.8 mmol). After stirring at ambient temperature for 2 h, the reaction mixture was diluted with EtOAc (40 mL) and H2O (3 mL). The layers were separated, the organic layer was washed with H2O (3×3 mL) and the combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (40 g silica gel column, eluting with 0-30% EtOAc/hexanes) to afford the sub-title compound (506 mg, 77%). LCMS (ESI) calc. for C15H23N4O4S [M+H-Boc+H]+ m/z=355.2. found 355.1

1. customThe layers were separated
2. washthe organic layer was washed with H2O (3×3 mL)
3. extractionthe combined aqueous phases were extracted with EtOAc (3 mL)
4. washThe combined organic layers were washed with brine (3 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by flash column chromatography (40 g silica gel column, eluting with 0-30% EtOAc/hexanes)