Reacción #42872

Ecuación de reacción

HCl

4-(5-phenyl-pentanoylamino)-thiophene-3-carboxylic acid methyl ester

LiOH

→

title compound

Rendimiento 43.7%

4-(5-Phenyl-pentanoylamino)-thiophene-3-carboxylic acid

Rendimiento 43.7%

Disolventes

tetrahydrofuran methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted two times with ethyl acetate
2. 2
   LavadoThe combined organic layers were washed with water and brine
3. 3
   Secadodried over sodium sulfate
4. 4
   OtroThe solvent was removed under reduced pressure
5. 5
   Otrothe crude product was purified by thin layer chromatography (SiO2, dichloromethane)

Procedimiento

To a solution of 4-(5-phenyl-pentanoylamino)-thiophene-3-carboxylic acid methyl ester (50 mg, 0.16 mmol) in tetrahydrofuran/methanol 2/1 (1.5 ml) was added a 1 N aqueous LiOH solution (0.95 ml, 0.95 mmol). The reaction mixture was stirred at room temperature for 2 h, acidified with 1 N HCl and extracted two times with ethyl acetate. The combined organic layers were washed with water and brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by thin layer chromatography (SiO2, dichloromethane) to give the title compound as colorless oil (20 mg, 0.07 mmol, 42%).

Fuente