An efficient synthesis of 1,3-bis(1,4,7-triazacyclonon-1-yl)-2-hydroxypropane, [1,3-bis(TACN)-2-propanol]

Abstract

An efficient synthesis of 1,3-bis(1,4,7-triazacyclonon-1-yl)-2-hydroxypropane is described. In contrast to earlier procedures, an improved synthetic strategy led to the selection of suitable reagents and conditions that afforded the title compound in excellent overall yield with improved process efficiency and scalability. Moreover, the mildness and synthetic efficiency of the chosen conditions were particularly well-suited for the large-scale synthesis of the title compound, which is in increasing demand for a variety of applications, including the preparation of stationary phases for immobilized metal-ion affinity chromatography of recombinant proteins.

Keywords:

• macrocyclic ligands
• 1,4,7-triazacyclononane (TACN)
• 1,3-bis(1,4,7-triazacyclonon-1-yl)-2-hydroxypropane
• efficient synthesis
• immobilized metal-ion affinity chromatography (IMAC)

Acknowledgements

We thank Dr. Kei Saito and Ms Sweta Pant for their useful discussions on TACN synthesis. This work was supported by the Australian Research Council.