Reaktion #1003325

ord-bf7a318a47654e2ea5f2443c575677bc

Reaktionsgleichung

COC(=O)[C@@H](N)Cc1ccc(O)cc1
L-tyrosine methyl ester
CC(=O)CC(=O)c1cccnc1
1-nicotinoylacetone
→
COC(=O)C(Cc1ccc(O)cc1)NC(C)=CC(=O)c1cccnc1
title compound
Ausbeute 79.0%
COC(=O)C(Cc1ccc(O)cc1)NC(C)=CC(=O)c1cccnc1
2-[1-methyl-3-oxo-3-(3-pyridyl)-propenylamino]-3-(4-hydroxyphenyl)-propionic acid methyl ester
Ausbeute 79.0%

Edukte

COC(=O)[C@@H](N)Cc1ccc(O)cc1
L-tyrosine methyl ester
CC(=O)CC(=O)c1cccnc1
1-nicotinoylacetone

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

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-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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07268157B2uspto-grants-2007_09