Improved synthesis of 10-(2-alkylamino-2-oxoethyl)-1,4,7,10- tetraazacyclododecane-1,4,7-triacetic acid derivatives bearing acid-sensitive linkers

Bhumasamudram Jagadish, Tarik J. Ozumerzifon, Sue A. Roberts, Gabriel B. Hall, Eugene A. Mash, Natarajan Raghunand

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Alkylation of the hydrobromide salts of 1,4,7-tris(methoxycarbonylmethyl)- 1,4,7,10-tetraazacyclododecane and 1,4,7-tris(ethoxycarbonylmethyl)-1,4,7,10- tetraazacyclododecane with appropriate α-bromoacetamides, followed by hydrolysis, provides convenient access to 10-(2-alkylamino-2-oxoethyl)-1,4,7,10- tetraazacyclododecane-1,4,7-triacetic acid derivatives that contain acid-sensitive functional groups. The utility of the method is demonstrated by improved syntheses of two known 1,4,7,10-tetraazacyclododecane-1,4,7,10- tetraacetic acid monoamides bearing acid-sensitive ω-tritylthio alkyl chains in much greater yields based on cyclen as the starting material. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

Original languageEnglish (US)
Pages (from-to)441-449
Number of pages9
JournalSynthetic Communications
Volume44
Issue number3
DOIs
StatePublished - Feb 1 2014

Keywords

  • Cyclen
  • DO3A monoamide
  • DOTA monoamide
  • medical imaging
  • synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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