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

Research output: Contribution to journalArticle

25 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2058-2061
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number17
DOIs
StatePublished - Apr 27 2011

Keywords

  • Contrast agent
  • DO3A
  • DOTA
  • MRI
  • Synthesis
  • X-ray crystallography

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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