Water → 2-oxo-3-tert-butoxycarbonylamino-5-acetyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine
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:24])[CH3:23].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:22](=[O:24])[CH3:23])[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
Product 1
Reagents, catalysts & solvents 1
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), acetyl chloride (0.56 ml) and pyridine (0.64 ml) were added thereto, the mixture was refluxed for 2 hours. Water (100 ml) was added, extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and diisopropyl ether was added to the residue for trituration, collectedly filtration, to thereby obtain 1.33 g of the titled compound.
Workup
- temperaturethe mixture was refluxed for 2 hours
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated aqueous sodium bicarbonate
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure, and diisopropyl ether
- additionwas added to the residue for trituration, collectedly filtration
Sources & evidence
- ORD record
- ord-c99b203c06d64710b83775dfd4be9acc
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06239131B1
Reaction notes
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