Pyridine → 2-oxo-3-tert-butoxycarbonylamino-5-(2,2-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979460Notes

Reaction equation

HRID 1979460 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].[CH3:22][C:23]([CH3:29])([CH2:27][CH3:28])[C:24](Cl)=[O:25].N1C=CC=CC=1.C(Cl)Cl>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:24](=[O:25])[C:23]([CH3:29])([CH3:22])[CH2:27][CH3:28])[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 1049PyridineHCID 6344DichloromethaneHCID 799582,2-Dimethylbutyryl chlorideHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015972-oxo-3-tert-butoxycarbonylamino-5-(2,2-dimethylbutanoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 89.8%

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 (1.0 g) was suspended in 1,2-dichloroethane (20 ml), and 2,2-dimethylbutanoyl chloride (538 mg) and pyridine (0.33 ml) were added thereto to the suspension, and the mixture was refluxed for 2 hours. Methylene chloride was added to the reaction mixture, washed with water and saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, crystals so precipitate were washed with ether, to thereby obtain 1.20 g of the title compound (Yield 89.8%).

Workup

  1. temperatureto the suspension, and the mixture was refluxed for 2 hours
  2. washwashed with water and saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure, crystals so precipitate
  5. washwere washed with ether

Sources & evidence

ORD record
ord-62e301874d2a4381887955c7a04ffd70
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

Loading…