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Tetrabutylammonium Fluoride → 8-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

HRID 558990
ノート
印刷プレビュー

反応式

HRID 558990 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([C:16]1[CH:47]=[CH:46][C:19]([CH2:20][NH:21][C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[F:34])[N:27]([CH2:35][CH2:36][O:37][Si](C(C)(C)C)(C)C)[C:26](=[O:45])[CH2:25]2)=[O:23])=[C:18]([CH3:48])[CH:17]=1)=[O:15].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([C:16]1[CH:47]=[CH:46][C:19]([CH2:20][NH:21][C:22]([N:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][C:32]=3[F:34])[N:27]([CH2:35][CH2:36][OH:37])[C:26](=[O:45])[CH2:25]2)=[O:23])=[C:18]([CH3:48])[CH:17]=1)=[O:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 670001684-[2-(tert-Butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

生成物 1

HCID 669995298-Fluoro-4-(2-hydroxyethyl)-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
2 回

実験手順

To a solution of 4-[2-(tert-butyldimethylsilanyloxy)ethyl]-8-fluoro-3-oxo-3,4-dihydro-2H-quinoxaline-1-carboxylic acid 4-[(2-furan-2-ylphenyl)methylcarbamoyl]-2-methylbenzylamide from Example 21F (0.34 mmol) in THF (5.0 ml) was added a solution of tetrabutylammonium fluoride in THF (1.0 M, 1.0 ml, 1.0 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 3 days. The mixture was evaporated in vacuo and the residue was taken up in CH2Cl2 and washed with ammonium chloride solution. The organic phase was dried and evaporated in vacuo and the residue was purified by flash chromatography on silica (eluant CHCl3:methanol 95:5) to give a white solid; yield 120 mg, 64%.

後処理

  1. temperaturewhile cooling in an ice/water bath
  2. customThe mixture was evaporated in vacuo
  3. washwashed with ammonium chloride solution
  4. customThe organic phase was dried
  5. customevaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica (eluant CHCl3:methanol 95:5)
  7. customto give a white solid

出典と根拠

ORDレコード
ord-6da342f1447f4d7791a8d75e572dd316
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063038B2

反応ノート

読み込み中…

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