反应详情

温度

100 °C

To a solution of Example 135C (1.7 g, 3.9 mmol) in toluene (15 mL) was added methyl trifluoromethanesulfonate (0.64 mL, 5.8 mmol). The mixture was warmed to 100° C. and stirred for 20 hours, cooled to ambient temperature and diluted with water (20 mL) and acetone (50 mL). This solution was allowed to stir for 30 minutes then concentrated NH4OH (10 mL) was added. The mixture was stirred for 30 minutes then partially concentrated under reduced pressure. The mixture was diluted with EtOAc (30 mL) and brine (10 mL) and the layers were separated. The aqueous phase was extracted with EtOAc (3×5 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 80% hexanes/EtOAc to 100% EtOAc to 10% MeOH in EtOAc) afforded the title compound (1.3 g, 2.9 mmol, 74% yield). MS (ESI−) m/z 454 (M+H)+.

1. temperaturecooled to ambient temperature
2. stirringto stir for 30 minutes
3. stirringThe mixture was stirred for 30 minutes
4. concentrationthen partially concentrated under reduced pressure
5. additionThe mixture was diluted with EtOAc (30 mL) and brine (10 mL)
6. customthe layers were separated
7. extractionThe aqueous phase was extracted with EtOAc (3×5 mL)
8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification by column chromatography (SiO2, 80% hexanes/EtOAc to 100% EtOAc to 10% MeOH in EtOAc)