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Hydrochloric Acid → 1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-acetyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979407
Notes
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Reaction equation

HRID 1979407 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[N:5]([C:14](=[O:16])[CH3:15])[CH2:4][CH:3]1[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])=[O:28].[OH-].[Na+].Cl>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:30]1([CH3:35])[C:29]([C:27]([CH2:26][N:8]2[C:7]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=3[N:5]([C:14](=[O:16])[CH3:15])[CH2:4][CH:3]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:2]2=[O:1])=[O:28])=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 124306762-Bromo-2'-methylacetophenoneHCID 212016002-oxo-3-tert-butoxycarbonylamino-5-acetyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212015901-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-acetyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine
Yield 79.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-5-acetyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.30 g) was suspended in toluene (18 ml), 2-bromo-2′-methylacetophenone (1.00 g), 1N aqueous sodium hydroxide (9 ml) and tetra n-butylammonium bromide (20 mg) were added thereto, and the mixture was stirred for 2 hours at room temperature. The reaction mixture was weakly acidified with 1N hydrochloric acid, extracted with methylene chloride. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue for trituration, collected by filtration, to thereby obtain 1.45 g of the titled compound (Yield: 79.7%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiisopropyl ether was added to the residue for trituration
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9d96bf6f7d3c4fc0aee2ba12104c494c
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06239131B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes