Triethylamine → Benzyl glycinate

Participants

Reaction Steps

As shown in scheme C, reaction of 3,4-dinitrobenzoic acid with thionyl chloride gave 3,4-dinitrobenzoyl chloride, which on further treatment with benzyl glycinate in the presence of triethylamine gave benzyl 2-(3,4-dinitrobenzamido)acetate (intermediate 3). The intermediate 3 is treated either with K18F or K19F in the presence of a catalyst such as kryptofix [2.2.2] or 18-crown-6 to yield benzyl 2-(4-fluoro-3-nitrobenzamido)acetate, which on reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave 2-(3-amino-4-fluorobenzamido)acetic acid (compound 3). In an analogous manner, 2-(5-amino-2-chloro-4-fluorobenzamido)acetic acid (compound 4) is synthesized starting from 2-chloro-4,5-dinitrobenzoic acid.

Provenance & Evidence