Water → 1-(2-nitrophenacyl)-2-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979326Notes

Reaction equation

HRID 1979326 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][CH:3]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[H-].[Na+].Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])=[O:32].O>CN(C)C=O>[N+:39]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C:31](=[O:32])[CH2:30][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][CH:3]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:2]1=[O:1])([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2440252-Bromo-2'-nitroacetophenoneHCID 21201812HCID 21201812, compound

Product 1

HCID 212016071-(2-nitrophenacyl)-2-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Oxo-3-tert-butoxycarbonylamino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (100 mg) was added to a suspension of 60% sodium hydride (22 mg) in N,N-dimethylformamide (5 ml), the mixture was stirred at room temperature for 15 minutes. Subsequently, 2-bromo-2′-nitroacetophenone (102 mg) was added thereto, and stirred at room temperature for one hour. Water was added to the reaction mixture, extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Isopropyl ether was added to the residue for trituration and collected by filtration, to thereby to obtain 76 mg of the title compound as a light yellow solid (Yield: 52%).

Workup

  1. stirringstirred at room temperature for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionIsopropyl ether was added to the residue for trituration
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ec02f634985b4b2abcadaa5b76cf84d7
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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