3-Ethoxy-2-methyl-3-oxopropane-1-diazonium → HCID 178438641、化合物

HRID 1412335

反応式

HRID 1412335 の反応式
[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]

参加物

5

反応物 2

HCID 866440353-Ethoxy-2-methyl-3-oxopropane-1-diazoniumHCID 178438592HCID 178438592、化合物

生成物 1

HCID 178438641HCID 178438641、化合物収率 89%

試薬・触媒・溶媒 2

HCID 178476747HCID 178476747、化合物触媒HCID 1140Toluene溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ca8e9613fa6e482d9d2e5e3cff3c4f77
出典データセット
uspto-grants-2014_12
特許番号
US08921379B2

関連ノート

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