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Sodium Hydroxide → 1-(2-Toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979434
ノート
印刷プレビュー

反応式

HRID 1979434 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=[O:4].[OH-].[Na+].[O:14]=[C:15]1[NH:21][C:20]2[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:19]=2[N:18]([C:27](=[O:33])[C:28]2[S:32][CH:31]=[CH:30][CH:29]=2)[CH2:17][CH:16]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:6]1([CH3:11])[C:5]([C:3]([CH2:2][N:21]2[C:20]3[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:19]=3[N:18]([C:27](=[O:33])[C:28]3[S:32][CH:31]=[CH:30][CH:29]=3)[CH2:17][CH:16]([NH:34][C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[C:15]2=[O:14])=[O:4])=[CH:10][CH:9]=[CH:8][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 124306762-Bromo-2'-methylacetophenoneHCID 212015632-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 212017551-(2-Toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine収率 96%

試薬・触媒・溶媒 2

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 1140Toluene溶媒

実験手順

2-Bromo-2′-methylacetophenone (0.51 g), 1N aqueous sodium hydroxide (20 ml), toluene (20 ml) and tetra n-butylammonium bromide (20 mg) were added to 2-Oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.80 g), the mixture was stirred at room temperature for 4 hours. The reaction mixture was separated into organic layer and aqueous layer, the aqueous layer was extracted with ethyl acetate, the extract was combined with the former organic layer. The combined extract was successively washed with water and 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(n-hexane:ethyl acetate=2:1), to thereby obtain 1.02 g of the title compound as colorless amorphous (Yield: 96%).

後処理

  1. customThe reaction mixture was separated into organic layer and aqueous layer
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas successively washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-05f997b964c24e4f822becac9d621f61
出典データセット
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06239131B1

反応ノート

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