3-Cyanobenzoic acid → N-[m-(m-cyanobenzamido)benzoyl]-beta-alanine benzyl ester

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Reaction Steps

For the preparation of the starting material, m.p. 182°-183° C., 3-cyanobenzoic acid and N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate are coupled to give N-[m-(m-cyanobenzamido)benzoyl]-β-alanine benzyl ester, MS: 428 (100, M+H), and this is converted with hydrogen sulphide and triethylamine in pyridine into N-[m-[m-(thiocarbamoyl)benzamido]benzoyl]-β-alanine benzyl ester, m.p. 128°-131° C. The latter is then reacted with methyl iodide in acetone and subsequently with ammonium acetate in methanol and treated with benzyl chloroformate and triethylamine in THF.

Provenance & Evidence