Sodium Carbonate → N-[[2-Amino-5-(2,4-dimethyl-1H-imidazol-1-yl)phenyl]methyl]glycine methyl ester

HRID 2231656Notes

Reaction equation

HRID 2231656 reaction equation
FC(F)(F)C([N:5]([CH2:12][C:13]1[CH:18]=[C:17]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]2[CH3:25])[CH:16]=[CH:15][C:14]=1[NH2:26])[CH2:6][C:7]([O:9][CH2:10]C)=[O:8])=O.C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:26][C:14]1[CH:15]=[CH:16][C:17]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]2[CH3:25])=[CH:18][C:13]=1[CH2:12][NH:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 21285544HCID 21285544, compound

Product 1

HCID 21285520N-[[2-Amino-5-(2,4-dimethyl-1H-imidazol-1-yl)phenyl]methyl]glycine methyl esterYield 40.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl N-trifluoroacetyl-N-(2-amino-5-[2,4-dimethylimidazol-1-yl]benzyl)glycinate (1.4 g) and anhydrous sodium carbonate (0.74 g) in methanol (20 cm3) was heated under reflux for 3 hours. The cooled solution was evaporaed to dryness in vacuo and the residue was partitioned between chloroform (50 cm3) and water (10 cm3). The aqueous phase was re-extracted with chloroform (2×25 cm3) and the combined and dried (MgSO4) organic extracts were evaporated to give an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade mark]), eluting with ethyl acetate:methanol, 9:1. Combination and evaporation of the appropriate fractions afforded the title compound as an oil (0.41 g), used directly.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customthe residue was partitioned between chloroform (50 cm3) and water (10 cm3)
  4. extractionThe aqueous phase was re-extracted with chloroform (2×25 cm3)
  5. dry with materialdried (MgSO4) organic extracts
  6. customwere evaporated
  7. customto give an oil which
  8. customwas chromatographed on silica (Merck "MK 60.9385" [Trade mark])
  9. washeluting with ethyl acetate
  10. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-5d1e2edadc6e424086ed87f4421f9c30
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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