Dimethyl 3-oxoglutarate → methyl 2-(5-oxo-1-(2-phenylpropan-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)acetate

HRID 244942

반응식

HRID 244942 반응식
[C:1]1([C:7]([NH:10][NH:11]C(OC(C)(C)C)=O)([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+].CO[C:38]([CH2:40][C:41]([CH2:43][C:44]([O:46][CH3:47])=[O:45])=O)=[O:39]>C(Cl)Cl.C(O)(=O)C.C(OCC)(=O)C>[O:39]=[C:38]1[N:10]([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([CH3:9])[CH3:8])[N:11]=[C:41]([CH2:43][C:44]([O:46][CH3:47])=[O:45])[CH2:40]1

참가 물질

8

반응물 4

HCID 74591Dimethyl 3-oxoglutarateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 19606120tert-Butyl 2-(2-phenylpropan-2-yl)hydrazinecarboxylate

생성물 1

HCID 86697465methyl 2-(5-oxo-1-(2-phenylpropan-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)acetate수율 35.1%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

tert-Butyl 2-(2-phenylpropan-2-yl)hydrazinecarboxylate (250 mg, 1.00 mmol) was dissolved in methylene chloride (2 mL), mixed with p-toluenesulfonic acid monohydrate (0.40 g, 2.1 mmol) and stirred at room temperature for 18 hours. The reaction solution was basified with saturated aqueous sodium hydrogen carbonate and separated. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in toluene (2.0 mL) and acetic acid (70 μL), mixed with dimethyl 1,3-acetonedicarboxylate (174 mg, 1.00 mmol) and stirred at 90° C. for 3 hours and at 105° C. for 3 hours. After completion of the reaction, the reaction solution was allowed to cool to room temperature and diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and then with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel12 g, ethyl acetate:hexane=1:9 to 3:7) to give 96.3 mg of the desired product as a white solid.

후처리

  1. customseparated
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in toluene (2.0 mL)
  7. stirringstirred at 90° C. for 3 hours and at 105° C. for 3 hours
  8. customAfter completion of the reaction
  9. temperatureto cool to room temperature
  10. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  11. dry with materialwith saturated aqueous sodium chloride, dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. customThe resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel12 g, ethyl acetate:hexane=1:9 to 3:7)

출처 및 근거

ORD 기록
ord-e1d33a0014ef49b0a544c1fb1f20cbf7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658686B2

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