Vol. 23 No. 3 (2024): Mapana Journal of Sciences
Research Articles

Isolation, characterization, and synthesis of some process-origin impurities of Atovaquone, a renowned anti-malarial drug

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  • Sanjay Sukumar Saralaya,
  • Shashikumar Somashekar Hiriyalu,
  • Akshaya Raghavendra Bhat,
  • Shashiprabha,
  • Shridhara Kanakamajalu
Sanjay Sukumar Saralaya
Sri Dharmasthala Manjunatheshwara Institute of Technology, Ujire, Karnataka, India
Shashikumar Somashekar Hiriyalu
Independent researcher
Akshaya Raghavendra Bhat
Independent Researcher
Shashiprabha
PG Department of Chemistry, Sri Dharmasthala Manjunatheshwara College (Autonomous), Ujire-574 240, Karnataka, India.
Shridhara Kanakamajalu
Chief Scientific Officer, BioOrganics & Applied Materials, Peenya Industrial Area, Bangalore
Bio
DOI: https://doi.org/10.12723/mjs.70.6

Published 2024-11-09

Keywords

  • Atovaquone,
  • 2,3-Dichloro-1,4-naphthoquinone,
  • Impurities,
  • Isolation,
  • Characterization,
  • Synthesis
    • ...More
    Less

Copyright (c) 2024

Creative Commons License

This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Abstract

To improve the yield of Atovaquone, we explored the chemical consequences occurring during its step-wise synthesis (process chemistry). Hence, the entire focus of this initiative was aimed towards the isolation of a few major process origin byproducts that were formed during the two-step reaction process. The synthesis of Atovaquone was done by the use of commercially viable key starting material trans-4-(4-chlorophenyl) cyclohexanecarboxylic acid for the decarboxylative coupling reaction with another key reactant 2,3-dichloro-1,4-naphthoquinone to obtain the intermediate. The isolated intermediate was hydrolyzed to obtain Atovaquone.  From the mother liquors (MLRs) of each stage, we were able to isolate a few major process origin impurities and characterize them with the assistance of spectral data. Additionally, we even synthesized some of the impurities and compared them with the ones that were isolated from the MLRs. In this work, we report the experimental aspects and results related to six process-origin impurities of Atovaquone. 

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References

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