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

HRID 1979410Notes

Reaction equation

HRID 1979410 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]([CH3:28])=[CH: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])[CH:24]=[C:23]([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 1023943-Methyl-2-butenoyl chlorideHCID 212015812-oxo-3-tert-butoxycarbonylamino-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015842-oxo-3-tert-butoxycarbonylamino-5-(3-methyl-2-butenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 63.2%

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) obtained from Referential Example 7 was suspended in 1,2-dichloroethane (40 ml), 3,3-dimethylacryloyl chloride (941 mg) and pyridine (626 mg) were added, the mixture was refluxed for one hour. The reaction mixture was allowed to cool, water (100 ml) was added, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Isopropylether was added to the residue for trituration, collected by filtration, to thereby obtain 1.62 g of the titled compound.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionIsopropylether was added to the residue for trituration
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d825c39c30b74e3e899e35f7ad4f697b
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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