Andreana Morandini
University Ca’ Foscari of Venice, Italy
Title: Study of the in situ formulation of Active Condensation Agents and their use for amide formation
Biography
Biography: Andreana Morandini
Abstract
The synthesis of covalent bonds for the formation of amides and esters is of great importance to produce pharmaceuticals, peptides, polymers, etc, these reactions often require a long time and hard conditions. A wide variety of condensing reagents is known such as acyl azides, uronium salts and carbodiimides can occur these reaction in a short time and at room temperature.
In the last decade, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride (DMTMM) has been demonstrated to be a very efficient condensing reagent and its use is rapidly increasing due to its high activity, high solubility in water and alcoholic solvents. New alternative condensing agents are of great interest for fine chemistry synthesis to reduce costs and improve yelds.
This in mind, we developed a protocol for the in situ preparation of a library of 4-(4,6-dialkoxy-1,3,5-triazin-2-yl)-4-alkyl-ammonium halides to be used as condensing agents for the formation of amide bonds. Our preliminary results show that these quaternary ammonium salts formulated in situ, further simplify the use of these reagents, reducing their cost. Moreover, in some cases the preformed quaternary ammonium salt is unstable and decomposes quickly while the in situ formulation gives an active and efficient condensing agent. Conversions of over 80% are achieved in most cases in around 15 min.
These activating agents have been efficiently employed for the synthesis of amides and the stabilization of collagen.