Pyridine → Ethyl 3-acetamido-2-oxobutanoate

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.

1. temperatureThe mixture was heated
2. temperatureto reflux
3. temperatureat reflux for a further 3 h
4. additionwas added
5. extractionthe mixture was extracted
6. washThe organic phase was washed with saturated aqueous sodium chloride solution
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated on a rotary evaporator
9. customThe crude mixture was reacted further without any further purification

ORD record

ord-128e4ba877f94bf5af5cdbccba9152a0

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434731B2