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

HRID 1979347Notes

Reaction equation

HRID 1979347 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].[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].N1C=CC=CC=1.O>C(Cl)Cl>[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:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[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 62493Pivaloyl chlorideHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015442-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 55.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (30.0 g) obtained from Referential Example 7 was dissolved in methylene chloride (300 ml), pivaloyl chloride (15.0 g) and pyridine (9.8 g) were added thereto, the mixture was refluxed for 2 hours and 30 minutes. The reaction mixture was allowed to cool, Water was added, and extracted with chloroform. The organic layer was successively washed with saturated aqueous sodium bicarbonate, water, and saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, to thereby obtain the 21.5 g of titled compound as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 2 hours and 30 minutes
  2. temperatureto cool
  3. extractionextracted with chloroform
  4. washThe organic layer was successively washed with saturated aqueous sodium bicarbonate, water, and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7885e3b36144437a9ddaec911ea60410
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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