L-Alanine → (S)-2-(2,6-dinitrobenzamido)propanoic acid

Participants

Reaction Steps

As shown in scheme 1,2,6-dinitrobenzoyl chloride prepared from 2,6-dinitrobenzoic acid is treated with L-alanine in the presence of sodium carbonate to yield (S)-2-(2,6-dinitrobenzamido)propanoic acid (intermediate 13). Treatment of intermediate 13 either with K18F or K19F gave (S)-2-(2-fluoro-6-nitrobenzamido)propanoic acid, which on reduction with iron powder in the presence of acetic acid gave (S)-2-(2-amino-6-fluorobenzamido)propanoic acid (compound 12). In an analogous manner, treatment of 2,6-dinitrobenzoyl chloride with D-alanine gave (R)-2-(2,6-dinitrobenzamido)propanoic acid (intermediate 14), which on treatment either with K18F or K19F and further reduction with iron powder gave (R)-2-(2-amino-6-fluorobenzamido)propanoic acid (compound 13).

Provenance & Evidence