3-Ethoxy-2-methyl-3-oxopropane-1-diazonium → HCID 178438641, 화합물

HRID 519621

반응식

HRID 519621 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][N:35]=[C:9]23)[CH2:4][CH2:3]1.C([O:38][C:39](=[O:45])[CH:40](C)[CH2:41][N+]#N)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Rh+]>[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:12]2[C:13](=[O:14])[N:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([O:1][CH:40]([CH3:41])[C:39]([OH:45])=[O:38])[CH2:3][CH2:4]3)[C:9]3[N:10]([N:33]=[CH:34][N:35]=3)[C:11]=2[CH2:30][CH2:31][CH3:32])=[CH:17][CH:18]=1)#[N:29]

참가 물질

5

반응물 2

HCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178438592HCID 178438592, 화합물

생성물 1

HCID 178438641HCID 178438641, 화합물수율 89%

시약·촉매·용매 2

HCID 178476747HCID 178476747, 화합물촉매HCID 1140Toluene용매2회

실험 절차

To a mixture of 4′-{[4-(trans-4-hydroxycyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (4 g), rhodium(I) acetate (0.028 g) and toluene (70 mL) was added dropwise a solution (10 mL) of 3-ethoxy-2-methyl-3-oxopropane-1-diazonium (5.5 mL) in toluene at 80° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was concentrated, and the obtained residue was purified by silica gel column chromatography. The obtained residue was dissolved in tetrahydrofuran (20 mL) and methanol (20 mL), and 1N aqueous sodium hydroxide solution (20 mL) was added. The reaction mixture was stirred for 1 hr, 1N aqueous hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate. The obtained 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 (4.1 g, 89%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe obtained residue was purified by silica gel column chromatography
  3. dissolutionThe obtained residue was dissolved in tetrahydrofuran (20 mL)
  4. additionmethanol (20 mL), and 1N aqueous sodium hydroxide solution (20 mL) was added
  5. stirringThe reaction mixture was stirred for 1 hr
  6. addition1N aqueous hydrochloric acid solution was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe obtained ethyl acetate layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1a9e26cb03544b168892c6f25fdac07f
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115136B2

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