Sodium hydride → HCID 21201702, compound

HRID 1979299Notes

Reaction equation

HRID 1979299 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]([C:17]23[CH2:26][CH:21]4[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]4)[CH2:18]2)[CH2:24]3)=[O:16])[CH2:6][CH:5]1[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].Br[CH2:36][C:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[CH3:45])=[O:38]>O1CCCC1>[C:40]1([CH3:45])[C:39]([C:37]([CH2:36][N:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]34[CH2:26][CH:21]5[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]5)[CH2:18]3)[CH2:24]4)=[O:16])[CH2:6][CH:5]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:4]2=[O:3])=[O:38])=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124306762-Bromo-2'-methylacetophenoneHCID 21201841HCID 21201841, compound

Product 1

HCID 21201702HCID 21201702, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 60% sodium hydride (128 mg) suspended in anhydrous tetrahydrofuran (30 ml), 2-oxo-3-tert-butoxycarbonylamino-5-(adamantan-1-yl)carbonyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine was added at room temperature under argon atmosphere. The mixture was stirred at room temperature for 30 minutes. Subsequently, 2-bromo-2′-methylacetophenone (375 mg) in anhydrous tetrahydrofuran (10 ml) was added thereto, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. Ice-water (50 ml) was added to the residue, followed by extraction with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Ethanol was added to the residue for solidification and collection by filtration, to thereby obtain 426 mg of the title compound as a white solid (yield: 46.6%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionIce-water (50 ml) was added to the residue
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. additionEthanol was added to the residue for solidification and collection by filtration

Sources & evidence

ORD record
ord-12b81889235c4844b36810b159773c93
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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