Dimethylformamide → HCID 67953938, compound

HRID 2402544Notes

Reaction equation

HRID 2402544 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]([O:15][C:16]1[CH:32]=[CH:31][C:19]2[N:20]([CH2:29][CH3:30])[C:21](=[O:28])[CH:22]([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]=2[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:33](I)[CH2:34][CH2:35][CH3:36]>C(OCC)(=O)C>[CH2:8]([O:15][C:16]1[CH:32]=[CH:31][C:19]2[N:20]([CH2:29][CH3:30])[C:21](=[O:28])[C:22]([CH2:33][CH2:34][CH2:35][CH3:36])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]=2[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 67954003HCID 67954003, compound

Product 1

HCID 67953938HCID 67953938, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under ice cooling, sodium hydride (60% in oil) (129 mg, 3.23 mmol) was added to a N,N-dimethylformamide (5 mL) solution of 7-benzyloxy-1-ethyl-3,5-dimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (500 mg, 1.48 mmol), and the mixture was stirred at 0° C. for 30 minutes. Thereafter, butyl iodide (0.336 mL, 2.95 mmol) was added. The reaction solution was stirred at 0° C. for 30 minutes, and then stirred at room temperature for 2 hours. The reaction solution was poured into ice water, and ethyl acetate (20 mL) extraction was performed. The resulting organic layer was washed with water, and the solvent was distilled off. The resulting residue was subjected to silica gel column chromatography (elution solvent: 1:2=ethyl acetate:n-hexane). The solvent was distilled off, thereby obtaining 520 mg of a colorless, liquid target compound (yield: 89%).

Workup

  1. stirringThe reaction solution was stirred at 0° C. for 30 minutes
  2. stirringstirred at room temperature for 2 hours
  3. washThe resulting organic layer was washed with water
  4. distillationthe solvent was distilled off
  5. washThe resulting residue was subjected to silica gel column chromatography (elution solvent: 1:2=ethyl acetate:n-hexane)
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8e7f3ab405f74cef81624612e6a07639
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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