On the Synthesis of 1,4,7-Tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

Bhumasamudram Jagadish; Gayle L Brickert-Albrecht; Gary S Nichol; Eugene A Mash; Natarajan Raghunand

doi:10.1016/j.tetlet.2010.10.074

On the Synthesis of 1,4,7-Tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

Tetrahedron Lett. 2011 Apr 27;52(17):2058-2061. doi: 10.1016/j.tetlet.2010.10.074.

Authors

Bhumasamudram Jagadish¹, Gayle L Brickert-Albrecht, Gary S Nichol, Eugene A Mash, Natarajan Raghunand

Affiliation

¹ Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721-0041.

Abstract

1,4,7-Tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane is widely used as an intermediate in the preparation of medically important DO3A and DOTA metal chelators. Despite its commercial availability and importance, the literature describing the preparation and properties of the free base is limited and sometimes unclear. We present herein an efficient synthesis of the hydrobromide salt of 1,4,7-tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane, characterize this compound spectroscopically and by X-ray crystallographic analysis, describe its simple conversion to the corresponding free base, characterize this compound spectroscopically and by X-ray crystallographic analysis, and make observations on the reactivity of this interesting and useful compound.

Abstract

Grants and funding