Hitting a Soft Drug with a Hard Nucleophile: Preparation of Esmolol's Metabolite by Treatment with Bis(tributyltin) Oxide

Abstract

A facile method for the production of esmolol's metabolite in high purity is described. Bis(tributyltin) oxide is used to disrupt esmolol's ester linkage, and hydrolysis is completed by addition of water, which also allows the inorganic side products to be conveniently extracted into ether. Evaporation of the aqueous phase and trituration with ethyl acetate provides the carboxylic acid–amine internal salt as a white, free-flowing powder.

GRAPHICAL ABSTRACT

Keywords:

• Bis(tributyltin) oxide
• esmolol metabolite
• ester hydrolysis
• synthesis