Reaktion #335875

Reaktionsgleichung

Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)-amino]benzoate

sodium hydroxide

citric acid

→

title compound

Ausbeute 76.7%

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

Ausbeute 76.7%

Lösungsmittel

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring further at room temperature overnight
2. 2
   workup.DISTILLATIONis distilled off under reduced pressure
3. 3
   workup.ADDITIONTo the residue is added water (50 ml)
4. 4
   Extraktionthe mixture is extracted with ethyl acetate
5. 5
   WaschenThe extract is washed with saturated aqueous sodium chloride solution
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent is distilled off under reduced pressure
8. 8
   SonstigeThe residue is purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
9. 9
   workup.ADDITIONThe fractions containing the desired compound
10. 10
    Sonstigeare collected
11. 11
    Einengenconcentrated under reduced pressure
12. 12
    Sonstigethe precipitates are separated by filtration

Vorschrift

Ethyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)-amino]benzoate (6.37 g) is dissolved in methanol (100 ml), and thereto is added 1 N aqueous sodium hydroxide solution (49.5 ml) under ice cooling, and the mixture is stirred for 2 hours under nitrogen. After stirring further at room temperature overnight, the reaction mixture is acidified with saturated aqueous citric acid solution, and methanol is distilled off under reduced pressure. To the residue is added water (50 ml), and the mixture is extracted with ethyl acetate. 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, and the precipitates are separated by filtration to give the title compound (4 g).

Quelle