1350800-77-9Relevant articles and documents
Kinetic and mechanistic insight into the thermodynamic degradation of saxagliptin
Jones, G. Scott,Savage, Scott A.,Ivy, Sabrina,Benitez, Patrick L.,Ramirez, Antonio
, p. 10332 - 10337 (2011)
The dipeptidyl peptidase-IV inhibitor saxagliptin (Onglyza) can undergo a thermodynamically favored cyclization to form the corresponding cyclic amidine. The kinetics and mechanism of this conversion were examined to develop a commercial synthesis that afforded saxagliptin with only trace levels of this key byproduct. Important findings of this work are the identification of a profound solvent effect and the determination of an autocatalytic pathway. Both of these phenomena result from transition structures involving proton transfer (Figure presented).