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The synthesis of N-[4-dimethylamino-1-butyl(1-13C)-N-nitrosobenzamide], an inhibitor of tryspin; Cyanide does not exchange with acetonitrile

✍ Scribed by Emil H. White; Yulong Chen

Publisher
John Wiley and Sons
Year
1993
Tongue
French
Weight
348 KB
Volume
33
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of N‐[4‐dimethylamino‐1‐butyl(1‐^13^C)‐N‐nitrosobenzamide], a powerful active‐site‐directed inhibitor of trypsin, is reported. An efficient use of ^13^C‐cyanide ion was achieved in the reaction with 1‐chloro‐3‐dimethylaminopropane, the first step of the synthesis. Acetonitrile was used as a co‐solvent with water in that step; no evidence was found for cyanide ion exchange with acetonitrile. The earlier report of such an exchange appears to be in error; the formation of hydrocyanic acid under the reaction conditions can account for the observations.

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