Methyl iodide → ethyl (2S)-2-(N-methylanilino)propanoate

HRID 2184071Notes

Reaction equation

HRID 2184071 reaction equation
[C:1]1([NH:7][C@H:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.Cl.C(OCC)(=O)C>[CH3:15][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C@H:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:9]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21124386ethyl (2S)-2-anilinopropanoate

Product 1

HCID 69800727ethyl (2S)-2-(N-methylanilino)propanoateYield 34%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl N-phenylalaninate (2 g, 10.3 mmol) in DMF (103 mL) was added powdered potassium carbonate (2.6 g, 18.5 mmol) followed by iodomethane (1.03 mL, 16.6 mmol) and the resulting mixture was heated at 70° C. over 3 days. The reaction mixture was cooled to room temperature and diluted with 1 M HCl and ethyl acetate. The product was extracted 3 times with ethyl acetate and the combined organics washed with brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (8:1 hexanes/EtOAc) yielded the title compound as a colorless oil (725 mg, 34%). MS (ES+) m/z 208 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted 3 times with ethyl acetate
  3. washthe combined organics washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (8:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-cd82dfc41bf84f2f9f59979e175b3228
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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