反应详情

温度

-78 °C

FTY 720 (310 mg, 1.00 mmol) was suspended in dry dichloromethane (10 mL) and cooled down to −78° C. Diethylaminosulfur trifluoride (DAST, 0.13 mL, 1.00 mmol, 1.0 eq.) was slowly added to this suspension and the mixture was allowed to warm up to r.t. overnight. The reaction was neutralized with saturated sodium bicarbonate solution (30 mL) at −10° C. The phases were separated and the aqueous phase was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, 20×3 cm, dichloromethane/methanol, 4:1) and subsequently by gradient HPLC (RP-HPLC Nucleodur 100-10 C18ec column (250×16 mm), acetonitrile/water (0.1% TFA)) with a Knauer HPLC system. The obtained TFA salt was dissolved in methanol (1 mL) and 1 M sodium hydroxide solution (3 mL) and the mixture was extracted with dichloromethane (5×5 mL). The organic phases were dried over Na2SO4 and concentrated. The product was dried in high vacuum and obtained as highly viscous oil. Yield: 5 mg (2%).

1. temperatureto warm up to r.t. overnight
2. customThe phases were separated
3. extractionthe aqueous phase was extracted with dichloromethane (3×20 mL)
4. dry with materialThe combined organic layers were dried over MgSO4
5. customthe solvent was removed under reduced pressure
6. customThe residue was purified by column chromatography (silica gel, 20×3 cm, dichloromethane/methanol, 4:1) and subsequently by gradient HPLC (RP-HPLC Nucleodur 100-10 C18ec column (250×16 mm), acetonitrile/water (0.1% TFA)) with a Knauer HPLC system
7. dissolutionThe obtained TFA salt was dissolved in methanol (1 mL)
8. extraction1 M sodium hydroxide solution (3 mL) and the mixture was extracted with dichloromethane (5×5 mL)
9. dry with materialThe organic phases were dried over Na2SO4
10. concentrationconcentrated
11. customThe product was dried in high vacuum
12. customobtained as highly viscous oil