Methyl iodide → Alanine, N-[4-(aminocarbonyl)-3-fluorophenyl]-2-methyl-, methyl ester

HRID 38754Notes

Reaction equation

HRID 38754 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[CH:6][C:5]=1[F:17])(=[O:3])[NH2:2].[C:18]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([CH3:15])([CH3:16])[C:12]([O:14][CH3:18])=[O:13])=[CH:6][C:5]=1[F:17])(=[O:3])[NH2:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666179022-((4-Carbamoyl-3-fluorophenyl)amino)-2-methylpropanoic acid

Product 1

HCID 66617687Alanine, N-[4-(aminocarbonyl)-3-fluorophenyl]-2-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

A solution of 2-(4-carbamoyl-3-fluorophenylamino)-2-methylpropanoic acid and K2CO3 (1.5 equivalents) in DMF (10 fold) was stirred at RT for 10 min. MeI (1.5 equivalents) was added and the reaction mixture was heated at 55-60° C. for 2 h. The solvent was removed under reduced pressure and the reaction mixture was poured in water, extracted with ethyl acetate (100 mL×2), dried over Na2SO4, concentrated and purified by column chromatography. 1H NMR (CDCl3, Freebase): δ (ppm) 7.9 (t, 1H), 6.5 (bs, 1H), 6.4 (d, 1H), 6.2 (d, 1H), 5.6 (bs, 1H), 4.6 (bs, 1H), 3.75 (s, 3H), 1.6 (s, 6H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe reaction mixture was poured in water
  3. extractionextracted with ethyl acetate (100 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-271f30e301a24d199343b3db95c1ef10
Source dataset
uspto-grants-2013_09
Patent number
US08524755B2

Reaction notes

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