Water → HCID 178438615, 화합물

HRID 519807

반응식

HRID 519807 반응식
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]3[N:33]=[CH:34][CH:35]=[C:9]23)[CH2:4][CH2:3]1.[N+](=[C:38]([CH3:44])[C:39](OCC)=O)=[N-].[C:45](OCC)(=O)[CH3:46].[OH2:51]>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[OH:51][C:38]([CH3:39])([CH3:44])[CH:45]([CH3:46])[O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=4)=[CH:18][CH:17]=3)=[C:11]([CH2:30][CH2:31][CH3:32])[N:10]3[N:33]=[CH:34][CH:35]=[C:9]23)[CH2:6][CH2:7]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 534409222-Diazonio-1-ethoxyprop-1-en-1-olateHCID 178438588HCID 178438588, 화합물

생성물 1

HCID 178438615HCID 178438615, 화합물수율 84%

시약·촉매·용매 2

HCID 168478Rhodium acetate촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4′-{[4-(trans-4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydropyrazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.70 g) and rhodium acetate (dimer, 0.066 g) in methylene chloride (5 mL) was added dropwise a solution of ethyl 2-diazopropanoate (1.0 g) in methylene chloride (2 mL), and the mixture was stirred for 18 hr. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was crudely purified by silica gel column chromatography. This was dissolved in tetrahydrofuran (5 mL), methylmagnesium bromide (1 M tetrahydrofuran solution, 3 mL) was added dropwise at 0° C., and the mixture was stirred for 1 hr. The mixture was diluted with ethyl acetate and then saturated aqueous ammonium chloride solution was added. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.45 g, 84%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crudely purified by silica gel column chromatography
  6. dissolutionThis was dissolved in tetrahydrofuran (5 mL)
  7. additionmethylmagnesium bromide (1 M tetrahydrofuran solution, 3 mL) was added dropwise at 0° C.
  8. stirringthe mixture was stirred for 1 hr
  9. additionThe mixture was diluted with ethyl acetate
  10. additionsaturated aqueous ammonium chloride solution was added
  11. extractionThe mixture was extracted with ethyl acetate
  12. washthe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated
  15. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d9164bc27ddf4eb0aa2ac91dff1a8865
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

연결된 노트

불러오는 중…