Sodium hydride → HCID 21201810, compound

HRID 1979348Notes

Reaction equation

HRID 1979348 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]([C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][CH:3]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[H-].[Na+].Br[CH2:31][C:32]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)=[O:33]>O1CCCC1>[C:34]1([C:32]([CH2:31][N:8]2[C:7]3[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=3[N:5]([C:14](=[O:19])[C:15]([CH3:18])([CH3:16])[CH3:17])[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:33])[S:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 212015442-oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 21201810HCID 21201810, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.0 g) was dissolved in tetrahydrofuran (10 ml), 60% sodium hydride (0.16 g) was added thereto under argon atmosphere, and the mixture was stirred for 30 minutes at room temperature. A solution of 2-bromoacetylthiophene (0.99 g) in tetrahydrofuran (1 ml) was added to the resultant mixture, stirred for 2 hours. The reaction mixture was poured into ice-water, extracted with ethyl acetate, the organic layer was washed succesively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 1.01 g of the titled compound (Yield: 76%).

Workup

  1. stirringstirred for 2 hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed succesively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ed4ee3b66c274df58377c50fd559cdb2
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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