Water → 2-oxo-3-tert-butoxycarbonylamino-5-cyclohexylcarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979423Notes

Reaction equation

HRID 1979423 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.N1C=CC=CC=1.O>ClCCCl>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([C:28]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:29])[CH2:4][CH:3]1[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 75938Cyclohexanecarbonyl chlorideHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015312-oxo-3-tert-butoxycarbonylamino-5-cyclohexylcarbonyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 74.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.00 g) was suspended in 1,2-dichloroethane (20 ml), cyclohexylcarbonyl chloride (1.21 g) and pyridine (652 mg) were added, and the mixture was refluxed for 1 hour and 30 minutes. Water (100 ml) was added to the reaction mixture, extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and n-hexane was added to the residue for trituration, collected by filtration, to thereby obtain 2.04 g of the titled compound (Yield: 74.2%).

Workup

  1. temperaturethe mixture was refluxed for 1 hour and 30 minutes
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure, and n-hexane
  6. additionwas added to the residue for trituration
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-00a41f4f7af04a0994b499c8db079428
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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