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

HRID 1979458Notes

Reaction equation

HRID 1979458 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-32a6eea953444157ba4a3832a251262d
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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