Methyl iodide → HCID 66732501, compound

HRID 2370356Notes

Reaction equation

HRID 2370356 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:10].[C:18]([O-])([O-])=O.[K+].[K+].CI>O>[F:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([CH3:17])([CH3:16])[C:13]([O:15][CH3:18])=[O:14])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66732622HCID 66732622, compound

Product 1

HCID 66732501HCID 66732501, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared according to General Method 5. A mixture of 2-(3-fluoro-4-(methoxymethyl)phenylamino)-2-methylpropanoic acid (1 g, 4.1 mmol), anhydrous K2CO3 (0.858 g, 6.2 mmol) and methyliodide (0.880 g, 6.2 mmol) was stirred at 60° C. for 3 h. The reaction mixture was diluted with water and extracted with ethyl acetate (20 mL×3), organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain crude product that was purified by silica gel chromatography (eluant 30% ethyl acetate-hexane) to obtain methyl 2-(3-fluoro-4-(methoxymethyl)phenylamino)-2-methylpropanoate.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with ethyl acetate (20 mL×3), organic layer
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain crude product that
  6. customwas purified by silica gel chromatography (eluant 30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3e00a8b6180b46a490ceae1641f85e41
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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