Unusual impurity formation during the process development of Olsalazine sodium leads to a new efficient and economical synthesis of tricaine mesylate

An impurity formation during the nitro group reduction for the synthesis of Olsalazine Sodium API, which was later explored for the development of a short and efficient manufacturing process for tricaine mesylate is reported here. The highlight of the synthesis is, during the nitro group reduction,...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2023-08, Vol.60 (8), p.1464-1473
Main Authors: Chaskar, Sudhir P., Honparkhe, Ramchandra, Chavan, Jagdish, Dhumal, Amit, Tripathy, Narendra K., Pramanik, Chinmoy, Chaudhari, Ashok, Thorat, Rakesh G., Gurjar, Mukund K.
Format: Article
Language:English
Subjects:
Deoxygenation
Impurities
Reduction
Sodium
Synthesis
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Summary:An impurity formation during the nitro group reduction for the synthesis of Olsalazine Sodium API, which was later explored for the development of a short and efficient manufacturing process for tricaine mesylate is reported here. The highlight of the synthesis is, during the nitro group reduction, the deoxygenation occurs forming the core of tricaine and the leaving mesyloxy group serves as a counter anion furnishing the tricaine mesylate in one step. The reported process here circumvents the need for isolation of the free base and a separate salt formation step, thus it is more economical and efficient.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4645