Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous flow technology

Submitting author affiliation:
Nelson Mandela Metropolitan University, University Way, Port Elizabeth, 6031, South Africa, Port Elizabeth, South Africa

Beilstein Arch. 2019, 201984.

Published 12 Aug 2019

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Tamiflu is one of the most effective anti-influenza drugs, which is currently manufactured by Hoffmann-La Roche from shikimic acid. Owing to its importance, more than 60 synthetic routes have been developed to date, however most of the synthetic routes utilise the potentially hazardous azide chemistry making them not green, thus not amenable to easy scale up. Consequently, this study exclusively demonstrated safe and efficient handling of potentially explosive azide chemistry involved in a proposed Tamiflu route by taking advantage of the continuous flow technology. The azide intermediates were safely synthesised in full conversions and >89 % isolated yields.  

Keywords: azide chemistry; continuous flow synthesis; hazardous; safe; Tamiflu

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Sagandira, C.; Watts, P. Beilstein Arch. 2019, 201984. doi:10.3762/bxiv.2019.84.v1

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