tetano
Editor, Senior Moderator
Beilstein J Org Chem. 2019 Oct 30;15:2577-2589. doi: 10.3762/bjoc.15.251. eCollection 2019. [h=1]Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology.[/h]
Sagandira CR[SUP]1[/SUP], Watts P[SUP]1[/SUP].
[h=3]Author information[/h] 1 Nelson Mandela University, University Way, Port Elizabeth, 6031, South Africa.
[h=3]Abstract[/h] 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.
Copyright ? 2019, Sagandira and Watts; licensee Beilstein-Institut.
[h=4]KEYWORDS:[/h] Tamiflu; azide chemistry; continuous flow synthesis; hazardous; safe
PMID: 31728172 PMCID: PMC6839569 DOI: 10.3762/bjoc.15.251
Free PMC Article
Sagandira CR[SUP]1[/SUP], Watts P[SUP]1[/SUP].
[h=3]Author information[/h] 1 Nelson Mandela University, University Way, Port Elizabeth, 6031, South Africa.
[h=3]Abstract[/h] 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.
Copyright ? 2019, Sagandira and Watts; licensee Beilstein-Institut.
[h=4]KEYWORDS:[/h] Tamiflu; azide chemistry; continuous flow synthesis; hazardous; safe
PMID: 31728172 PMCID: PMC6839569 DOI: 10.3762/bjoc.15.251
Free PMC Article