Model Based Approach to Develop a Ring-Closure Reaction with High Product Selectivity

Source: AIChE
  • Type:
    Conference Presentation
  • Conference Type:
    AIChE Annual Meeting
  • Presentation Date:
    November 12, 2015
  • Duration:
    30 minutes
  • Skill Level:
  • PDHs:

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An intramolecular nucleophilic aromatic substitution reaction promoted by strong base is a commonly used reaction to form pharmaceutically-relevant heterocycles in the industry.  In this contribution, modeling of this ring-closure reaction was used to achieve extremely high product selectivity over impurity formation by a competitive side reaction between the desired product and the strong base, potassium tert-butoxide. The elementary steps of this competitive reaction were investigated using in situ NMR techniques for raw data collection to derive a mechanistic kinetic model. Demonstration of the model findings, specifically removal of the byproduct t-butanol (t-BuOH) from the solution, resulted in reduced impurity formation.

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