Water → HCID 21201828, compound

HRID 1979400Notes

Reaction equation

HRID 1979400 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])([CH3:28])[CH2:24][C:25](Cl)=[O:26].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:25](=[O:26])[CH2:24][C:23]([CH3:29])([CH3:28])[CH3:22])[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 815143,3-Dimethylbutanoyl chlorideHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 21201828HCID 21201828, compoundYield 94.6%

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) obtained from Referential Example 7 was suspended in 1,2-dichloroethane (40 ml), 3,3-dimethylbutanoyl chloride (1.07 g) and pyridine (627 mg) were added, and the mixture was refluxed for 2 hours. Water was added to the reaction mixture, separated, the organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure, to thereby obtain 2.53 g of the titled compound (Yield: 90.1%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customseparated
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-30db1f16a00a4e90bda3c1c467b817d6
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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