Trifluoroacetic anhydride → HCID 178438712, 화합물

HRID 519636

반응식

HRID 519636 반응식
C([C:4]1([CH2:8][O:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([N:16]3[C:21](=[O:22])[C:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]5[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:26][C:25]=4[F:38])=[C:19]([CH2:39][CH2:40][CH3:41])[N:18]4[N:42]=[CH:43][N:44]=[C:17]34)[CH2:12][CH2:11]2)[CH2:7][CH2:6][CH2:5]1)(=O)C.O.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:51].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:38][C:25]1[CH:26]=[C:27]([C:30]2[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:28]=[CH:29][C:24]=1[CH2:23][C:20]1[C:21](=[O:22])[N:16]([C@H:13]2[CH2:14][CH2:15][C@H:10]([O:9][CH2:8][C:4]3([OH:51])[CH2:7][CH2:6][CH2:5]3)[CH2:11][CH2:12]2)[C:17]2[N:18]([N:42]=[CH:43][N:44]=2)[C:19]=1[CH2:39][CH2:40][CH3:41]

참가 물질

7

반응물 5

HCID 9845Trifluoroacetic anhydrideHCID 24477Sodium ThiosulfateHCID 449047Hydrogen peroxide waterHCID 516892Sodium BicarbonateHCID 178438710HCID 178438710, 화합물

생성물 1

HCID 178438712HCID 178438712, 화합물수율 65%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  1. customat room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in tetrahydrofuran (5 mL)
  7. additionmethanol (5 mL), 1N aqueous sodium hydroxide solution (5 mL) was added
  8. stirringthe mixture was stirred at room temperature for 30 min
  9. addition1N Aqueous hydrochloric acid solution was added to the reaction mixture
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-cc7648658f784e92a5ddf862b3fb64e1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

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