Sodium hydride → HCID 21201907, compound

HRID 1979443Notes

Reaction equation

HRID 1979443 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+].[CH3:30][C:31]1[O:35][C:34]([C:36](=[O:39])[CH2:37]Br)=[CH:33][CH:32]=1>O1CCCC1>[CH3:30][C:31]1[O:35][C:34]([C:36]([CH2:37][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:39])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 111171262-Bromo-1-(5-methylfuran-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 21201907HCID 21201907, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Oxo-3-tert-butoxycarbonylamino-5-pivaloyl-8-methyl-1,3,4,5-tetrabydro-2H-1,5-benzodiazepine (1.0 g) obtained from Step 1 of Example 89 was dissolved in tetrahydrofuran (10 ml), under argon atmosphere 60% sodium hydride (0.16 g) was added, and the mixture was stirred at room temperature for 30 minutes. Subsequently, a solution of 5-methyl-2-bromoacetylfuran (1.23 g) in tetrahydrofuran (1 ml) was added to the mixture, stirred at room temperature for 30 minutes. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=3:1), to thereby obtain 0.89 g of the title compound.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f99c4b77d4364338af0f6f1636a63e6e
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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