Reaktion #606966

Reaktionsgleichung

trifluoroacetic acid anhydride

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

hydrogen peroxide

sodium hydrogen carbonate

sodium thiosulfate

→

title compound

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

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   workup.ADDITIONTo a solution of the obtained residue in tetrahydrofuran (3 mL)-methanol (3 mL) was added 2 N aqueous sodium hydroxide solution (2 mL)
7. 7
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
8. 8
   Extraktionextracted with ethyl acetate
9. 9
   WaschenThe extract was washed with saturated brine
10. 10
    Trocknendried over anhydrous magnesium sulfate
11. 11
    SonstigeThe solvent was evaporated under reduced pressure
12. 12
    Sonstigethe residue was purified by basic silica gel chromatography [eluent: hexane/ethyl acetate=60/406→35/65 (volume ratio)]

Vorschrift

To a mixture of 4′-{[4-(trans-3-acetylcyclobutyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3′-fluorobiphenyl-2-carbonitrile (1.38 g), 30% aqueous hydrogen peroxide solution (13.85 mL) and chloroform (20 mL) was added trifluoroacetic acid anhydride (7.66 mL), and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution and sodium thiosulfate were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the obtained residue in tetrahydrofuran (3 mL)-methanol (3 mL) was added 2 N aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was acidified with 1 N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by basic silica gel chromatography [eluent: hexane/ethyl acetate=60/406→35/65 (volume ratio)] to give the title compound as a colorless amorphous compound (0.90 g, 69%).

Quelle