تفاعل #606818

معادلة التفاعل

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

المردود 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

المردود 65.0%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىat room temperature
2. 2
   استخلاصthe mixture was extracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with saturated brine
4. 4
   تجفيفdried over anhydrous magnesium sulfate
5. 5
   أخرىThe 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
    استخلاصthe mixture was extracted with ethyl acetate
11. 11
    غسيلThe ethyl acetate layer was washed with saturated brine
12. 12
    تجفيفdried over anhydrous magnesium sulfate
13. 13
    أخرىThe solvent was evaporated under reduced pressure
14. 14
    أخرىThe obtained residue was purified by silica gel column chromatography

الإجراء التجريبي

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%).

المصدر