Triethylamine → Benzoyl chloride, 2-chloro-5-nitro-

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Reaction Steps

As shown in scheme E, reaction of 2-chloro-5-nitrobenzoic acid with thionyl chloride gave 2-chloro-5-nitrobenzoyl chloride, which on further treatment with benzyl glycinate in the presence of triethylamine gave benzyl 2-(2-chloro-5-nitrobenzamido)acetate (intermediate 6). Treatment of intermediate 6 either with K18F or K19F in the presence of kryptofix [2.2.2] or 18-crown-6 to yield benzyl 2-(2-fluoro-5-nitrobenzamido)acetate, which on further reduction with hydrogen gas or hydrogen source in the presence of Pd/C gave 2-(5-amino-2-fluorobenzamido)acetic acid (compound 5).

Provenance & Evidence