Acetone → 4'-{[4-(3-Hydroxy-1,5-dioxaspiro[5.5]undec-9-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 1412387ノート

反応式

HRID 1412387 の反応式
C=[C:2]1[CH2:7][O:6][C:5]2([CH2:12][CH2:11][CH:10]([N:13]3[C:18](=[O:19])[C:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:23][CH:22]=4)=[C:16]([CH2:35][CH2:36][CH3:37])[N:15]4[N:38]=[CH:39][N:40]=[C:14]34)[CH2:9][CH2:8]2)[O:4][CH2:3]1.I([O-])(=O)(=O)=[O:42].[Na+].CC(C)=O.C(#N)C>[Os](=O)(=O)(=O)=O.O.C(OCC)(=O)C>[OH:42][CH:2]1[CH2:3][O:4][C:5]2([CH2:8][CH2:9][CH:10]([N:13]3[C:18](=[O:19])[C:17]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([C:27]5[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=5)=[CH:25][CH:26]=4)=[C:16]([CH2:35][CH2:36][CH3:37])[N:15]4[N:38]=[CH:39][N:40]=[C:14]34)[CH2:11][CH2:12]2)[O:6][CH2:7]1

参加物

8

反応物 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 23667635Sodium periodate2 回HCID 670089314'-{[4-(3-Methylidene-1,5-dioxaspiro[5.5]undec-9-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

生成物 1

HCID 670088804'-{[4-(3-Hydroxy-1,5-dioxaspiro[5.5]undec-9-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile収率 74.4%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒2 回HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 4′-{[4-(3-methylidene-1,5-dioxaspiro[5.5]undec-9-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (2.0 g), sodium periodate (4.1 g), acetone (40 mL), acetonitrile (40 mL) and water (40 mL) was added osmium tetraoxide (1.48 g, 7% immobilized catalyst) at 0° C., and the mixture was stirred at room temperature for 8 hr. Sodium periodate (1.6 g) and osmium tetraoxide (0.60 g, 7% immobilized catalyst) were added, and the mixture was further stirred at room temperature for 16 hr. Ethyl acetate and water were added to the reaction mixture, the precipitate was filtered off, and the filtrate 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, and the residue was dissolved in tetrahydrofuran (10 mL) and methanol (20 mL), sodium tetrahydroborate (0.29 g) was added, and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture. After evaporation of the solvent under reduced pressure, the residue 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, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.5 g, 73%).

後処理

  1. stirringthe mixture was further stirred at room temperature for 16 hr
  2. filtrationthe precipitate was filtered off
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
  8. additionmethanol (20 mL), sodium tetrahydroborate (0.29 g) was added
  9. stirringthe mixture was stirred at room temperature for 2 hr
  10. additionSaturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture
  11. customAfter evaporation of the solvent under reduced pressure
  12. extractionthe residue was extracted with ethyl acetate
  13. washThe organic layer was washed with saturated brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customThe solvent was evaporated under reduced pressure
  16. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a30680734ce64cde970dc82a5c2f5883
出典データセット
uspto-grants-2014_12
特許番号
US08921379B2

反応ノート

読み込み中…