3-Bromocyclohexene → 2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1698765Notes

Reaction equation

HRID 1698765 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])O.[Na+].Br[CH:27]1[CH2:32][CH2:31][CH2:30][CH:29]=[CH:28]1>CN(C)C=O>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:32]2[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]2)[CH2:4][CH:3]1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 1370573-BromocyclohexeneHCID 516892Sodium BicarbonateHCID 154908313-Tert-butoxycarbonylamino-1,3,4,5-tetrahydrobenzo[b][1,4]diazepin-2-one

Product 1

HCID 154908322-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (±)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (28.6 g) in N,N-dimethylformamide (50 mL), sodium hydrogencarbonate (17.3 g) and 3-bromocyclohexene (33.2 g) were added, followed by LZ stirring at 50° C. for 1 hour. The reaction mixture was allowed to cool down. Subsequent to addition of ice water, the reaction mixture was extracted with methylene chloride. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue for crystallization. Crystals so precipitated were then collected by filtration. The crystals were washed with ethanol and then dried, whereby the title compound (30.1 g) was obtained. Yield: 82%.

Workup

  1. temperatureto cool down
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the residue for crystallization
  7. customCrystals so precipitated
  8. filtrationwere then collected by filtration
  9. washThe crystals were washed with ethanol
  10. customdried

Sources & evidence

ORD record
ord-a30db0b43fd04d3c8eafac02d251395c
Source dataset
uspto-grants-2002_02
Patent number
US06344452B1

Reaction notes

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