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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
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HRID 1979434 반응식
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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 74236
Tetrabutylammonium Bromide
촉매
HCID 1140Toluene용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-05f997b964c24e4f822becac9d621f61
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06239131B1

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