Reaktion #335876

Reaktionsgleichung

hydrochloric acid

3-Aminobenzoic acid

triethylamine

2-acetylthiomethyl-3-phenylpropionyl chloride

→

title compound

Ausbeute 41.3%

3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoic acid

Ausbeute 41.3%

Lösungsmittel

water

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture is stirred for 30 minutes and further at room temperature three nights
2. 2
   Extraktionextracted with chloroform
3. 3
   WaschenThe extract is washed with saturated aqueous sodium chloride solution
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent is distilled off under reduced pressure
6. 6
   SonstigeThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
7. 7
   workup.ADDITIONThe fractions containing the desired compound
8. 8
   Sonstigeare collected
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe precipitates are separated by filtration
11. 11
    Sonstigerecrystallized from 50% aqueous ethanol

Vorschrift

3-Aminobenzoic acid (1.4 g) is suspended in chloroform (50 ml), and thereto is added triethylamine (2.06 g), and to the mixture is added 2-acetylthiomethyl-3-phenylpropionyl chloride (2.61 g) with stirring under ice cooling, and the mixture is stirred for 30 minutes and further at room temperature three nights. To the reaction mixture is added water, and the mixture is acidified with hydrochloric acid and extracted with chloroform. The extract is washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated under reduced pressure. The precipitates are separated by filtration and recrystallized from 50% aqueous ethanol to give the title compound (1.5 g).

Quelle