反应详情

To a solution of benzyl (4-{[1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl]oxy}-2-fluorophenyl)carbamate (28.0 g) in tetrahydrofuran (280 mL) was added trifluoroacetic acid anhydride (196 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogen carbonate and saturated brine in this order, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, ethanol (140 mL) and 4N aqueous sodium hydroxide solution (40 mL) were added to the residue, and the mixture was stirred at room temperature for 4 hr. The solvent was concentrated under reduced pressure to 1/3, water was added to the residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1→9/1) to give the title compound (12.1 g, 51%).

1. customThe solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran
2. additionwas added to the residue
3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate and saturated brine in this order
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customThe solvent was evaporated under reduced pressure, ethanol (140 mL) and 4N aqueous sodium hydroxide solution (40 mL)
7. additionwere added to the residue
8. stirringthe mixture was stirred at room temperature for 4 hr
9. concentrationThe solvent was concentrated under reduced pressure to 1/3, water
10. additionwas added to the residue
11. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
12. washThe organic layer was washed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltered
15. customThe solvent was evaporated under reduced pressure
16. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=10/1→9/1)