Methyl iodide → HCID 66732959, compound

HRID 2370350Notes

Reaction equation

HRID 2370350 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH3:19])([CH3:18])[C:15]([OH:17])=[O:16])=[CH:9][C:8]=1[F:20])=[O:6])[CH2:2][CH3:3].[C:21]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[CH2:1]([NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH3:19])([CH3:18])[C:15]([O:17][CH3:21])=[O:16])=[CH:9][C:8]=1[F:20])=[O:6])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66732558HCID 66732558, compound

Product 1

HCID 66732959HCID 66732959, compoundYield 76.3%

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-(propylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid (1.0 g, 3.54 mmol) and K2CO3 (1.0 g, 7.2 mmol) in DMF (7 mL) was stirred at RT for 10 minutes. Methyl iodide (0.8 g, 5.6 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, dried over Na2SO4, concentrated and purified with column chromatography to obtain 800 mg of methyl 2-(4-(propylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoate.

Workup

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

Sources & evidence

ORD record
ord-65fb8c4a49c74df881cd2eec5916acaa
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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