Methyl iodide → HCID 66732832, compound

HRID 2370349Notes

Reaction equation

HRID 2370349 reaction equation
[C: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])([CH3:4])([CH3:3])[CH3:2].[C:22]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[C: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])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66731962HCID 66731962, compound

Product 1

HCID 66732832HCID 66732832, compoundYield 29.3%

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-(tert-butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid (1.0 g, 3.3 mmol) and K2CO3 (1.38 g, 10 mmol) in DMF (10 mL) was stirred at RT for 10 minutes. Methyl iodide (710 mg, 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 300 mg of methyl 2-(4-(tert-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-48068b81da604f44b5f5d65bf744beb1
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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