Methyl iodide → HCID 57678071, compound

HRID 491822Notes

Reaction equation

HRID 491822 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:11][C:10]=1[C:26]#[N:27])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:31]I.[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:31])=[CH:11][C:10]=1[C:26]#[N:27])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57678048HCID 57678048, compound

Product 1

HCID 57678071HCID 57678071, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyl(4-benzyloxycarbonylamino-2-cyanophenoxy)acetate (100 mg) obtained in Reference Example 50(2) is dissolved in N,N-dimethylformamide (3 ml) and thereto is added 60% oleaginous sodium hydride (12.5 mg). After the mixture is stirred for 20 minutes at room temperature, methyl iodide (24.4 μl) is added thereto dropwise and the mixture is further stirred for one hour. To the reaction solution is poured saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer is washed successively with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 followed by 3/1) to give t-butyl[4-(N-benzyloxycarbonyl-N-methylamino)-2-cyanophenoxy]acetate (91 mg).

Workup

  1. stirringdropwise and the mixture is further stirred for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed successively with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent
  7. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1 followed by 3/1)

Sources & evidence

ORD record
ord-700f9307445841b29fd25e450c029dd6
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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