反应 #606818

反应方程式

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

收率 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

收率 65.0%

溶剂

chloroform

反应条件

后处理

1. 1
   其他at room temperature
2. 2
   萃取the mixture was extracted with ethyl acetate
3. 3
   洗涤The organic layer was washed with saturated brine
4. 4
   干燥dried over anhydrous magnesium sulfate
5. 5
   其他The 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
    萃取the mixture was extracted with ethyl acetate
11. 11
    洗涤The ethyl acetate layer was washed with saturated brine
12. 12
    干燥dried over anhydrous magnesium sulfate
13. 13
    其他The solvent was evaporated under reduced pressure
14. 14
    其他The obtained residue was purified by silica gel column chromatography

实验过程

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%).

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