Reaktion #335850

Reaktionsgleichung

3-Amino-5-methylbenzoic acid

triethylamine

2-acetylthiomethyl-3-phenyl-propionyl chloride

→

title compound

Ausbeute 51.8%

3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]-5-methylbenzoic acid

Ausbeute 51.8%

Lösungsmittel

—

aqueous solution

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for 2 hours
2. 2
   workup.DISTILLATIONTetrahydrofuran is distilled off under reduced pressure
3. 3
   Extraktionthe residue is extracted with ethyl acetate (100 ml)
4. 4
   WaschenThe extract is washed with saturated aqueous sodium chloride solution
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONethyl acetate is distilled off under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue is dissolved in acetonitrile
8. 8
   Sonstigepurified 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 into dryness under reduced pressure

Vorschrift

3-Amino-5-methylbenzoic acid (1.9 g) is dissolved in a 60% aqueous solution of tetrahydrofuran (30 ml) containing triethylamine (2.3 g), and to the mixture is added dropwise a solution of 2-acetylthiomethyl-3-phenyl-propionyl chloride (3.2 g) in tetrahydrofuran (20 ml) with stirring under ice cooling, and the mixture is stirred at room temperature for 2 hours. Tetrahydrofuran is distilled off under reduced pressure, and the residue is extracted with ethyl acetate (100 ml). The extract is washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and then ethyl acetate is distilled off under reduced pressure. The residue is dissolved in acetonitrile and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected and concentrated into dryness under reduced pressure to give the title compound (2.4 g).

Quelle