Synthesis and crystal structure of topiramate azido-sulfate at 90 K and 298 K

Prabhakar Priyanka; Bidarur K Jayanna; Haruvegowda Kiran Kumar; Vinaya; Thayamma R Divakara; Hemmige S Yathirajan; Christopher Glidewell; Sean Parkin

doi:10.1107/S2056989022008799

Synthesis and crystal structure of topiramate azido-sulfate at 90 K and 298 K

Acta Crystallogr E Crystallogr Commun. 2022 Sep 8;78(Pt 10):984-988. doi: 10.1107/S2056989022008799. eCollection 2022 Oct 1.

Authors

Prabhakar Priyanka¹, Bidarur K Jayanna¹, Haruvegowda Kiran Kumar², Vinaya², Thayamma R Divakara³, Hemmige S Yathirajan², Christopher Glidewell⁴, Sean Parkin⁵

Affiliations

¹ Department of Chemistry, B. N. M. Institute of Technology, Bengaluru-560 070, India.
² Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.
³ T. John Institute of Technology, Bengaluru-560 083, India.
⁴ School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK.
⁵ Department of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA.

Abstract

The low (90 K) and room (298 K) temperature crystal structures of topiramate azido-sulfate [systematic name 2,3:4,5-bis-O-(1-methyl-ethyl-idene)-β-d-fructo-pyran-ose azido-sulfate], C₁₂H₁₉N₃O₈S, an inter-mediate in the synthesis of the anti-convulsant drug topiramate, are described. Topiramate azido-sulfate (I) finds use as a reference impurity standard for topiramate. A modified synthesis and some spectroscopic details are also presented.

Keywords: absolute configuration; anti-convulsant; crystal structure; intermediate; topiramate azidosulfate.

Grants and funding

HSY is grateful to the UGC, New Delhi for a BSR Faculty Fellowship for three years. The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732) and by the University of Kentucky.