Functionalized cyclic carbonate monomers prepared from 2,2-bis(methylol)propionic acid (bis-MPA) are widely used precursors for the synthesis of biocompatible polymers.  The cyclic carbonate monomer precursor can be functionalized through its ester linkage via an esterification reaction of the carboxylic acid precursor with the desired alcohol, with this transformation typically accomplished through use of an acid chloride intermediate.  In contrast, direct esterification methods utilizing the cyclic carbonate carboxylic acid precursor, alcohol, and a coupling reagent represent an advantage in terms of synthetic simplicity.  While N,N'-dicyclohexylcarbodiimide (DCC) has been used for this transformation it is often difficult to remove the DCC byproducts, and the use of alternative coupling reagents that cleanly produce the ester product would be advantageous.  We report investigation of the use of alternative coupling reagents for the esterification reaction including TBTU, COMU, and HATU.  Despite the reported effectiveness of these reactions in related ester bond forming reactions, they were not found to be effective in the esterification of carboxylic acid-containing cyclic carbonate monomers derived from bis-MPA.

Investigation of coupling reagents for esterification reactions of carboxylic acid-containing cyclic carbonate monomers

2019 Spring National Meeting

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