Hydrogen Peroxide → HCID 178438612, 화합물

HRID 1412507노트

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HRID 1412507 반응식
C([C:4]1([CH:8]([O:10][CH:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:22](=[O:23])[C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]5[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:27][CH:26]=4)=[C:20]([CH2:39][CH2:40][CH3:41])[N:19]4[N:42]=[CH:43][N:44]=[C:18]34)[CH2:13][CH2:12]2)[CH3:9])[CH2:7][CH2:6][CH2:5]1)(=O)C.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:50].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[OH:50][C:4]1([CH:8]([O:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([N:17]3[C:22](=[O:23])[C:21]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]5[C:32]([C:37]#[N:38])=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:29][CH:30]=4)=[C:20]([CH2:39][CH2:40][CH3:41])[N:19]4[N:42]=[CH:43][N:44]=[C:18]34)[CH2:15][CH2:16]2)[CH3:9])[CH2:5][CH2:6][CH2:7]1

참가 물질

7

반응물 5

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 670091324'-[(4-{4-[1-(1-Acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

생성물 1

HCID 178438612HCID 178438612, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
60 °C

실험 절차

To a mixture of 4′-[(4-{4-[1-(1-acetylcyclobutyl)ethoxy]cyclohexyl}-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (9.20 g), 30% aqueous hydrogen peroxide solution (77.5 mL) and chloroform (80 mL) was added trifluoroacetic acid anhydride (42.8 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 1 M 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 (15 mL)-methanol (15 mL) was added 2 N aqueous sodium hydroxide solution (15 mL), and the mixture was stirred at room temperature for 2 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 silica gel chromatography [eluent: hexane/ethyl acetate=80/20→40/60 (volume ratio)] to give the title compound as a colorless amorphous compound (1.45 g, 17%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo a solution of the obtained residue in tetrahydrofuran (15 mL)-methanol (15 mL) was added 2 N aqueous sodium hydroxide solution (15 mL)
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure
  12. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→40/60 (volume ratio)]

출처 및 근거

ORD 기록
ord-d52a1e9535f2443596d26c40197b76b4
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921379B2

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