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Abstract
Boronic acid and boronic pinacol ester functionalized compounds are the basis for Suzuki coupling and Petasis reactions that are widely used in pharmaceutical synthetic schemes. The purity analysis of these compounds utilizing traditional reversed phase liquid chromatography methodology is complicated by the potential of on‐column hydrolysis. Therefore, a fast liquid chromatography method was developed to minimize on‐column hydrolysis effects. The method was applied as an in‐process control method for the separation of three process related impurities from a boronic pinacol ester functionalized intermediate with no appreciable on‐column hydrolysis observed. The method was then optimized to successfully resolve ten different boronic acid and boronic pinacol ester functionalized compounds within five minutes. Thus, the wide range applicability of fast liquid chromatographic technology to this specific class of compounds was demonstrated.
Acknowledgments
The authors would like to thank Dr. Lushi Tan for providing amide boronic pinacol ester intermediate and its process related impurities in this work, and Dr. Richard Thompson for valuable discussions.