Methyl iodide → HCID 58008044, compound

HRID 1667646Notes

Reaction equation

HRID 1667646 reaction equation
[C:1]([C:5]1[CH:36]=[CH:35][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[NH:28][C:29](=[O:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CI.[C:39](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>O.C(#N)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][CH:18]=3)=[CH:13][C:12]=2[N:28]([CH3:39])[C:29](=[O:34])[C:30]([O:32][CH3:33])=[O:31])=[CH:35][CH:36]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 58007715HCID 58007715, compound

Product 1

HCID 58008044HCID 58008044, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl N-{4-[4-(tert-butyl)benzyloxy]-4′-(trifluoromethoxy)biphenyl-3-yl}oxamate (compound of Example 6 (4); 3.0 g, 5.982 mmol), methyl iodide (9.387 g, 66.180 mmol), potassium carbonate (2.480 g, 17.946 mmol), 18-crown-6 (158 mg, 0.598 mmol) and acetonitrile (50 ml) was stirred at 85° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (3.066 g, 99.4%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation of the solvent under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-4bf372f8a12a4f0f9c51185ebbef9bc1
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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