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

HRID 916143

Reaktionsgleichung

Reaktionsgleichung von HRID 916143
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bf7a318a47654e2ea5f2443c575677bc
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268157B2

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