Reaktion #1003322

Reaktionsgleichung

L-tyrosine methyl ester

1-(4-fluorobenzoyl)acetone

→

title compound

Ausbeute 96.0%

2-[1-methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester

Ausbeute 96.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is heated
2. 2
   Temperaturto reflux for 24 h
3. 3
   SonstigeThe solvent is evaporated under a vacuum
4. 4
   workup.ADDITIONTo the residue is added ethanol (50 ml)
5. 5
   workup.DISTILLATIONthe ethanol is distilled off under atmospheric pressure
6. 6
   SonstigeThe crude product is purified by silica gel chromatography

Vorschrift

To a solution of L-tyrosine methyl ester (4.00 g, 20.51 mmol) in methanol (150 ml) is added 1-(4-fluorobenzoyl)acetone (4.06 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 (7.03 g, 96%).

Quelle