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

HRID 1979434Notes

Reaction equation

HRID 1979434 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])=[O:4].[OH-].[Na+].[O:14]=[C:15]1[NH:21][C:20]2[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:19]=2[N:18]([C:27](=[O:33])[C:28]2[S:32][CH:31]=[CH:30][CH:29]=2)[CH2:17][CH:16]1[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:6]1([CH3:11])[C:5]([C:3]([CH2:2][N:21]2[C:20]3[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:19]=3[N:18]([C:27](=[O:33])[C:28]3[S:32][CH:31]=[CH:30][CH:29]=3)[CH2:17][CH:16]([NH:34][C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[C:15]2=[O:14])=[O:4])=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 124306762-Bromo-2'-methylacetophenoneHCID 212015632-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 212017551-(2-Toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-Bromo-2′-methylacetophenone (0.51 g), 1N aqueous sodium hydroxide (20 ml), toluene (20 ml) and tetra n-butylammonium bromide (20 mg) were added to 2-Oxo-3-tert-butoxycarbonylamino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.80 g), the mixture was stirred at room temperature for 4 hours. The reaction mixture was separated into organic layer and aqueous layer, the aqueous layer was extracted with ethyl acetate, the extract was combined with the former organic layer. The combined extract was successively washed with water and saturated brine, and 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=2:1), to thereby obtain 1.02 g of the title compound as colorless amorphous (Yield: 96%).

Workup

  1. customThe reaction mixture was separated into organic layer and aqueous layer
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas successively washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-05f997b964c24e4f822becac9d621f61
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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