Water → HCID 57835000, compound

HRID 730565Notes

Reaction equation

HRID 730565 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:9][CH2:10][O:11][C:12]1[C:20]2[NH:19][C:18](=[O:21])[N:17]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:32]I.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:9][CH2:10][O:11][C:12]1[C:20]2[N:19]([CH3:32])[C:18](=[O:21])[N:17]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57834990HCID 57834990, compound

Product 1

HCID 57835000HCID 57835000, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [2-(1-benzyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester (0.100 g, 0.252 mmol) in 2 mL of anhydrous N,N-dimethylformamide was added sodium hydride (11 mg of a 60% dispersion in mineral oil) under nitrogen. The suspension was stirred at room temperature for ten minutes and then methyl iodide (0.018 mL, 0.277 mmol) was added in one portion. Stirring was continued for one hour and the reaction mixture was added to 150 mL water, and extracted twice with 75 mL ethyl acetate. The combined organic fraction was washed with 100 mL brine, dried over sodium sulfated and concentrated in vacuo. The residue was purified by flash chromatography (18% to 28% ethyl acetate in hexane) to afford 92 mg (0.223 mmol, 88.5%) of [2-(1-benzyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-4-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester as a clear oil. MS: 412 (M+H)+.

Workup

  1. stirringStirring
  2. extractionextracted twice with 75 mL ethyl acetate
  3. washThe combined organic fraction was washed with 100 mL brine
  4. dry with materialdried over sodium
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (18% to 28% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b2783764a8c14c9095042c9d14634d55
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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