Water → 1-(N-tert-butyl)carbamoylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979458노트

반응식

HRID 1979458 반응식
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][CH:3]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[C:27]([NH:31][C:32](=[O:35])[CH2:33]Br)([CH3:30])([CH3:29])[CH3:28].[OH-].[Na+].O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[C:27]([NH:31][C:32]([CH2:33][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][CH:3]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:2]1=[O:1])=[O:35])([CH3:30])([CH3:29])[CH3:28]

참가 물질

8

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5863742-Bromo-N-(tert-butyl)acetamideHCID 154908332-Oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

생성물 1

HCID 212016631-(N-tert-butyl)carbamoylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine수율 83%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

2-Oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.0 g) was suspended in toluene (25 ml), N-tert-butyl-2-bromoacetamide (1.14 g), 1N aqueous sodium hydroxide (15 ml) and tetra n-butylammonium bromide (90 mg) were added thereto, and the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, separated. The aqueous layer was extracted with ethyl acetate, the ethyl acetate extract was combined with the former organic layer, and the combined extract was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, ether was added to the residue for trituration, collected by filtration, to thereby obtain 1.09 g of the title compound (Yield: 83.0%).

후처리

  1. customseparated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionthe ethyl acetate extract
  4. extractionthe combined extract
  5. washwas washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure, ether
  8. additionwas added to the residue for trituration
  9. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-32a6eea953444157ba4a3832a251262d
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06239131B1

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