The molecule 4-amino-3-phenylbutanoic acid contains amino and carboxy terminal groups. The reactivity of both groups was utilized for preparation of corresponding tetrazole-containing derivatives. The terminal amino group was directly replaced by a tetrazol-1-yl fragment through reaction of 4-amino-3-phenylbutanoic acid hydrochloride with triethyl orthoformate and sodium azide in acetic acid. 4-Amino-3-phenylbutanoic acid was converted into 4-(tetrazol-1-yl)-3phenylbutanoic acid and also methyl 4-(5-methyltetrazol-1-yl)-3-phenylbutanate in 79 and 45% yields, respectively.

4-amino-3-phenylbutanoic acid can be converted into 4-(tetrazol-1-yl)-3phenylbutanoic acid and methyl 4-(5-methyltetrazol-1-yl)-3-phenylbutanate with high yields.

Paper

Tetrazole-containing derivatives of 4-amino-3-phenylbutanoic acid

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