Tyrosine Methyl Ester → 2-[1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester

HRID 916143

Reaction equation

HRID 916143 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[NH2:5].[C:15]([CH2:23][C:24]([CH3:26])=O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1>CO>[CH3:1][O:2][C:3](=[O:14])[CH:4]([NH:5][C:24]([CH3:26])=[CH:23][C:15](=[O:22])[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 70652Tyrosine Methyl EsterHCID 3001601-(Pyridin-3-yl)butane-1,3-dione

Product 1

HCID 671332772-[1-Methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of L-tyrosine methyl ester (4.00 g, 20.51 mmol) in methanol (150 ml) is added 1-nicotinoylacetone (3.68 g, 22.56 mmol), then the mixture is heated to reflux for 24 h. The solvent is evaporated under a vacuum. To the residue is added ethanol (50 ml), then the ethanol is distilled off under atmospheric pressure. The crude product is purified by silica gel chromatography using hexane/EtOAc (4:1) as eluent to give the title compound (5.51 g, 79%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 24 h
  3. customThe solvent is evaporated under a vacuum
  4. additionTo the residue is added ethanol (50 ml)
  5. distillationthe ethanol is distilled off under atmospheric pressure
  6. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-bf7a318a47654e2ea5f2443c575677bc
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Linked notes

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