Studies in Tetrazole Chemistry. IV. Tetrazolylacetic Acids and Esters¹

Abstract

A method has been developed for the synthesis of 5-substituted-l-tetrazolylacetic esters and acids and a series of these compounds has been prepared. Several l-substituted-5-tetrazolylacetic acids have also been prepared by this method but substituted tetrazolylcarboxylates could not be isolated. Some comparative properties of the 1-and 5-tetrazolylacetic acids are briefly discussed.

The synthesis of [1‐14C]2‐(1H‐tetrazol‐5‐yl)acetic acid

“…A fourth possibility eliminated the need to form the tetrazole ring system by starting with 5‐methyl‐1 H ‐tetrazole. After protecting the nitrogen in the tetrazole ring system, the carbon‐14 could be incorporated by reacting with phenyl lithium, phenyl sodium, or butyl lithium and [ 14 C]carbon monoxide or its electrophilic equivalent . The resulting product could be hydrolyzed and the nitrogen could be deprotected to give [1‐ 14 C]2‐(1 H ‐tetrazol‐5‐yl)acetic acid shown in Scheme .…”

“…After protecting the nitrogen in the tetrazole ring system, the carbon-14 could be incorporated by reacting with phenyl lithium, phenyl sodium, 20 or butyl lithium 21 and [ 14 C]carbon monoxide 20 or its electrophilic equivalent. 21 The resulting product could be hydrolyzed and the nitrogen could be deprotected to give [1-14 C]2-(1H-tetrazol-5-yl)acetic acid shown in Scheme 4. This route was discarded because our laboratories are not suited to efficiently work with gaseous radioactive carbon monoxide.…”

Discovery of a Dual SENP1 and SENP2 Inhibitor

“…Mp 171–178 °C decomp. [Lit [ 45 ]: 180–182 °C]; 1 H-NMR (500 MHz, (CD 3 ) 2 SO): δ 13.75 (br s, 1H), 7.78–7.74 (m, 2H), 7.67–7.59 (m, 3H), 5.51 (s, 2H). 13 C-NMR (126 MHz, (CD 3 ) 2 SO): δ 167.7, 154.6, 131.4, 129.3, 128.4, 123.5, 49.1.…”