Methyl iodide → HCID 66732402, compound

HRID 2370348Notes

Reaction equation

HRID 2370348 reaction equation
[CH2:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])=[CH:10][C:9]=1[F:21])=[O:7])[CH2:2][CH2:3][CH3:4].[C:22]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[CH2:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH3:20])([CH3:19])[C:16]([O:18][CH3:22])=[O:17])=[CH:10][C:9]=1[F:21])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66732569HCID 66732569, compound

Product 1

HCID 66732402HCID 66732402, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

The title compound was prepared according to General Method 5. A solution of 2-(4-(butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid (900 mg, 3.04 mmol) and K2CO3 (1.38 mg, 10 mmol) in DMF (10 mL) was stirred at RT for 10 minutes. Methyl iodide (647 mg, 4.5 mmol) was added and heated at 55° C. for 4 h. The solvent was removed and reaction mixture was poured in water, extracted with ethyl acetate (100 mL, 2 times), dried over Na2SO4, concentrated and purified with column chromatography to obtain 400 mg of methyl 2-(4-(butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoate.

Workup

  1. customThe title compound was prepared
  2. customThe solvent was removed
  3. customreaction mixture
  4. extractionextracted with ethyl acetate (100 mL, 2 times)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified with column chromatography

Sources & evidence

ORD record
ord-ecc9a6c018d747309022a8ecd6f7351e
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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