反应详情

温度

-78 °C

Trifluoromethanesulfonic anhydride (0.85 mL, 5.1 mmol) was added to a solution of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (1 g, 3 mmol) (Aldrich, Cat 469106) and triethylamine (1 mL, 10 mmol) in methylene chloride (30 mL) at −78° C. The reaction was stirred for 1 h. at −78° C. Saturated NaHCO3 was added and the reaction was extracted with dichloromethane. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) to obtain (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid methyl ester (1.2 g, 80%) as light yellow oil. Analytical LCMS (M+H-Boc)+: m/z=327.9.

1. extractionthe reaction was extracted with dichloromethane
2. washThe organic phase was washed with saturated brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe crude product was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)