Reacción #532002

Ecuación de reacción

acetylalanine

pyridine

ethyl acetate

→

Ethyl 3-acetamido-2-oxobutanoate

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux
3. 3
   Temperaturaat reflux for a further 3 h
4. 4
   workup.ADDITIONwas added
5. 5
   Extracciónthe mixture was extracted
6. 6
   LavadoThe organic phase was washed with saturated aqueous sodium chloride solution
7. 7
   Secadodried over sodium sulfate
8. 8
   Concentraciónconcentrated on a rotary evaporator
9. 9
   OtroThe crude mixture was reacted further without any further purification

Procedimiento

52 g (396 mmol) of acetylalanine were dissolved in 800 ml of THF, and 45 mg (0.4 mmol) of 4-dimethylaminopyridine and 96 ml (1188 mmol) of pyridine were added. The mixture was heated to reflux, and 88 ml (792 mmol) of ethyl oxalyl chloride were added dropwise over a period of 45 min. The mixture was stirred at reflux for a further 3 h. The reaction mixture was added to ice-water, ethyl acetate was added and the mixture was extracted. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. The crude mixture was reacted further without any further purification.

Fuente