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

Participants

Reaction Steps

To a solution of L-alanine-methyl ester hydrochloride (1.68 g, 12.0 mmol, 1.1 equiv) and triethylamine (3.32 mL, 24.0 mmol 2.2 equiv) in DMF (20 mL) was added a solution of 2,6-dichloro-2-nitro-pyridine (2.14 g, 11.0 mmol, 1.0 equiv) in DMF (6 mL) and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was poured onto water and the product was extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-30%) to afford (S)-2-(6-chloro-3-nitro-pyridin-2-ylamino)-propionic acid methyl ester (1.9 g). MS: [M+H]+=260.

Provenance & Evidence