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

HRID 1180560
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HRID 1180560 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 33.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a 0° C. solution of methyl 1-acetyl-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate (9.8 g, 23.42 mmol) in methylene chloride (50 ml) was added, dropwise, a 1.0 molar solution of boron tribromide (51.52 ml, 51.52 mmol) in methylene chloride and the mixture was stirred overnight at room temperature. Ice and water were added to the reaction mixture and the insolubles filtered off. The filtrate was diluted with methylene chloride and water. The organic layer was separated, washed with saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give a crude product, which was purified by chromatography on silica gel (hexane:ethyl acetate (I:1)) to give 3.2 g of product as a white foam.

후처리

  1. filtrationthe insolubles filtered off
  2. additionThe filtrate was diluted with methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give a crude product, which
  8. customwas purified by chromatography on silica gel (hexane:ethyl acetate (I:1))

출처 및 근거

ORD 기록
ord-fc38c17b31f94de080cc30040653c89a
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07282496B2

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