On the Synthesis of 1,4,7-Tris(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane |
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Authors: | Jagadish Bhumasamudram Brickert-Albrecht Gayle L Nichol Gary S Mash Eugene A Raghunand Natarajan |
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Institution: | a Department of Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721-0041, United States b Department of Radiology, University of Arizona, Tucson, AZ 85724-5024, United States |
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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. |
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Keywords: | Synthesis DOTA DO3A Contrast agent MRI X-ray crystallography |
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