Process for the preparation of 5-substituted 1-tetrazole acetic acid esters or the corresponding acids.

摘要

1435809 1 - H - Tetrazole - -1 - acetate esters and acids ELI LILLY & CO 13 Aug 1973 [14 Aug 1972] 38132/73 Heading C2C Novel tetrazolylacetate esters and acids having the general formula wherein R is a (C 1 -C 12 ) hydrocarbon radical free from aliphatic unsaturation, a (C 1 -C 12 ) hydrocarbon -O- radical free from aliphatic unsaturation or an -O- alkali metal radical; and RSP1/SP is hydrogen, an alkali metal cation or a (C 1 -C 12 ) alkyl, (C 4 -C 8 ) cycloalkyl, phenyl, behzyl, p-nitrophenyl, p-nitrobenzyl, 2,2,2-trichloroethyl or phenacyl radical, as well those compounds of the above formula wherein RSP1/SP may also be tolyl, xylyl or phenylethyl, are prepared by reacting an acyl cyanide of the formula (II) with an azidoacetic acid or ester thereof having the formula (III) at a temperature of from 80‹ to 135‹ C. The resultant tetrazolylacetate ester may be further reacted with either (a) an alcoholic alkali metal hydroxide to form the corresponding alkali metal salt, (b) a base to remove the 5-acyl substituent and form the alkali metal salt of 1-tetrazoleacetic acid, provided that R is a (C 1 -C 12 ) hydrocarbon radical, or (c) with an acid to remove the 5-acyl substituent and form the 1-tetrazoleacetic acid, provided that R is a (C 1 -C 12 ) hydrocarbon -O- radical.