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Sodium Hydroxide → 1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979428
Notes
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Reaction equation

HRID 1979428 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]([CH:14]2[CH2:19][CH2:18][CH2:17][CH:16]=[CH:15]2)[CH2:4][CH:3]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].Br[CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])=[O:31].[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:33]1([CH3:38])[C:32]([C:30]([CH2:29][N:8]2[C:7]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=3[N:5]([CH:14]3[CH2:19][CH2:18][CH2:17][CH:16]=[CH:15]3)[CH2:4][CH:3]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:2]2=[O:1])=[O:31])=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 124306762-Bromo-2'-methylacetophenoneHCID 212015412-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexene-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212017491-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 39.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 1140TolueneSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.05 g) obtained from Step 1 of Referential Example 10 was dissolved in toluene (14 ml), 2-bromo-2′-methylacetophenone (723 mg), 1N aqueous sodium hydroxide (7 ml) and tetra n-butylammonium bromide (20 mg) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was separated into organic layer and aqueous layer, the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=5:1), to thereby obtain 557 mg of the titled compound.

Workup

  1. customThe reaction mixture was separated into organic layer and aqueous layer
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-656d78ec2f7049769f061bafd1212451
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