Reaktion #606818

Reaktionsgleichung

4′-[(4-{trans-4-[(1-acetylcyclobutyl)methoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]-3′-fluorobiphenyl-2-carbonitrile

hydrogen peroxide water

sodium hydrogen carbonate

sodium thiosulfate

trifluoroacetic acid anhydride

→

title compound

Ausbeute 65.0%

3′-fluoro-4′-[(4-{trans-4-[(1-hydroxycyclobutyl)methoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

Ausbeute 65.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   workup.DISSOLUTIONThe obtained residue was dissolved in tetrahydrofuran (5 mL)
7. 7
   workup.ADDITIONmethanol (5 mL), 1N aqueous sodium hydroxide solution (5 mL) was added
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature for 30 min
9. 9
   workup.ADDITION1N Aqueous hydrochloric acid solution was added to the reaction mixture
10. 10
    Extraktionthe mixture was extracted with ethyl acetate
11. 11
    WaschenThe ethyl acetate layer was washed with saturated brine
12. 12
    Trocknendried over anhydrous magnesium sulfate
13. 13
    SonstigeThe solvent was evaporated under reduced pressure
14. 14
    SonstigeThe obtained residue was purified by silica gel column chromatography

Vorschrift

To a mixture of 4′-[(4-{trans-4-[(1-acetylcyclobutyl)methoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]-3′-fluorobiphenyl-2-carbonitrile (0.3 g), 30% hydrogen peroxide water (2.1 g) and chloroform (10 mL) was gradually added trifluoroacetic acid anhydride (2.1 mL) at room temperature, and the reaction mixture was warmed to 60° C. and stirred for 24 hr. Saturated aqueous sodium hydrogen carbonate and sodium thiosulfate were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (5 mL) and methanol (5 mL), 1N aqueous sodium hydroxide solution (5 mL) was added, and the mixture was stirred at room temperature for 30 min. 1N Aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.19 g, 65%).

Quelle