Triethylamine → N-(6-Chloro-3-nitro-2-pyridyl)-alanine methyl ester

Participants

Reaction Steps

L-Alanine methyl ester hydrochloride (8.4 g, 0.06 mol) was dissolved in 100 ml of anhydrous N,N-dimethylformamide, and 16.6 ml (0.12 mol) of triethylamine were added. Subsequently, while stirring vigorously, 10.7 g (0.05 mol) of 2,6-dichloro-3-nitropyridine in 20 ml of anhydrous N,N-dimethylformamide were slowly added dropwise, during which the reaction temperature rose above 40° C. After a further 3 h at room temperature, the reaction mixture was poured into about 400 ml of ice-water, extracted three times with ethyl acetate, dried (sodium sulfate) and concentrated. After chromatography on silica gel (ethyl acetate/heptane=1:5 then 1:2), 9.0 g (69%) of compound A were isolated as a yellow oil,

Provenance & Evidence