Sodium hydride → HCID 21201777, compound

HRID 1979295Notes

Reaction equation

HRID 1979295 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:5]1[NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39])=[O:32]>O1CCCC1>[C:34]1([CH3:39])[C:33]([C:31]([CH2:30][N:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][CH:5]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:4]2=[O:3])=[O:32])=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124306762-Bromo-2'-methylacetophenoneHCID 21201812HCID 21201812, compound

Product 1

HCID 21201777HCID 21201777, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride (1.6 g) was suspended in tetrahydrofuran (100 ml), 2-Oxo-3-tert-butoxycarbonylamino-5-pivaloyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (7.23 g) was added thereto under ice-cooling, and the resultant mixture was stirred for one hour. Subsequently, 2-bromo-2′-methylacetophenone (4.88 g) was added thereto, and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. Ice-water was added to the residue. The resultant mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 7.8 g of the title compound (yield: 79%)

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionIce-water was added to the residue
  4. extractionThe resultant mixture was extracted with methylene chloride
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8a43a90cab3d4da1a0706c0373e363c4
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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