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Water → Methyl 1-Acetyl-4-(4-hydroxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate

HRID 1264609
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HRID 1264609 반응식
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:6]([C:26]([O:28][CH3:29])=[O:27])[CH2:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br.O>C(Cl)Cl>[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:6]([C:26]([O:28][CH3:29])=[O:27])[CH2:5]1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 18612735HCID 18612735, 화합물

생성물 1

HCID 18612782Methyl 1-Acetyl-4-(4-hydroxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate수율 77.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a cooled (0°) solution of 2.0 g (4.78 mmol) of methyl 1-acetyl-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate in 14 ml of CH2Cl2 was added dropwise 143.3 ml (14.3 mmol) of a 1.0 molar solution of BBr3 in CH2Cl2. The mixture was stirred at room temperature for 1.5 hours. Ice and H2O were added to the reaction mixture and the insolubles filtered off. The filtrate was diluted with CH2Cl2 and H2O and the CH2Cl2 layer separated, washed with brine and dried (Na2 SO4) The solvent was removed under vacuum to give 1.5 g of a white foam. The solid was chromatographed on silica gel with hexane-ethyl acetate (1:1) as solvent to give a foam which was dried under vacuum to give 0.52 g of product as a white foam; Anal. Calc'd for C19H20N2O6S: C, 56 4;H, 5.0; N, 6.9; Found: C 55.1; H, 4.7; N, 6.5.

후처리

  1. filtrationthe insolubles filtered off
  2. additionThe filtrate was diluted with CH2Cl2 and H2O
  3. customthe CH2Cl2 layer separated
  4. washwashed with brine
  5. customdried (Na2 SO4) The solvent
  6. customwas removed under vacuum

출처 및 근거

ORD 기록
ord-0c7d1f8377c640009a5db50746281e83
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06544984B1

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