ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethyl Sulfoxide → HCID 136063915、化合物

HRID 1412679
ノート
印刷プレビュー

反応式

HRID 1412679 の反応式
[Cl-].O[NH3+:3].[C:4](=[O:7])([O-])[OH:5].[Na+].CS(C)=O.[Si]([O:20][CH:21]([CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1)[CH2:22][N:23]1[C:28](=[O:29])[C:27]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]3[C:38]([C:43]#[N:44])=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:33][CH:32]=2)=[C:26]([CH2:45][CH2:46][CH3:47])[N:25]2[N:48]=[C:49]([CH3:51])[N:50]=[C:24]12)(C(C)(C)C)(C)C>O.C(OCC)(=O)C>[CH:52]1([CH:21]([OH:20])[CH2:22][N:23]2[C:28](=[O:29])[C:27]([CH2:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[C:43]4[NH:44][C:4](=[O:7])[O:5][N:3]=4)=[CH:35][CH:36]=3)=[C:26]([CH2:45][CH2:46][CH3:47])[N:25]3[N:48]=[C:49]([CH3:51])[N:50]=[C:24]23)[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 67008779HCID 67008779、化合物

生成物 1

HCID 136063915HCID 136063915、化合物収率 86.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
50 °C

実験手順

A mixture of hydroxylammonium chloride (1.3 g), sodium hydrogen carbonate (2.1 g) and dimethyl sulfoxide (10 mL) was stirred at 50° C. for 30 min, 4′-{[4-(2-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclohexylethyl)-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (0.76 g) was added, and the mixture was stirred at 90° C. for 20 hr. After allowing to cool to room temperature, 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, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography, and dissolved in tetrahydrofuran (15 mL). N,N′-Carbonyldiimidazole (0.24 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 N hydrochloric acid and then 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). Tetrabutylammonium fluoride (1 M tetrahydrofuran solution, 3.1 mL) was added and the mixture was stirred at 70° C. for 5 hr. The reaction mixture was extracted with ethyl acetate and water, and the organic layer was washed with water and then 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 amorphous solid (0.6 g, 86%).

後処理

  1. stirringthe mixture was stirred at 90° C. for 20 hr
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. dissolutiondissolved in tetrahydrofuran (15 mL)
  9. additionN,N′-Carbonyldiimidazole (0.24 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 mL) were added
  10. stirringthe mixture was stirred at room temperature for 2 hr
  11. additionThe reaction mixture was diluted with ethyl acetate
  12. washwashed with 1 N hydrochloric acid
  13. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
  16. additionTetrabutylammonium fluoride (1 M tetrahydrofuran solution, 3.1 mL) was added
  17. stirringthe mixture was stirred at 70° C. for 5 hr
  18. extractionThe reaction mixture was extracted with ethyl acetate and water
  19. washthe organic layer was washed with water
  20. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  21. customThe solvent was evaporated under reduced pressure
  22. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bec2da8e092f4d6f9d4e728509617983
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921379B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート