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Topic: Azidation of Tosylate  (Read 691 times)

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Offline watizit97

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Azidation of Tosylate
« on: November 02, 2019, 12:34:29 AM »

I’d like to combine two molecule components via Huisgen reaction but unfortunately I’m unable to convert my tosylate to azide. Does anyone have any idea on how to solve this problem? Any advices would be greatly appreciated.

*Please refer to the attached photo to have a look on the chemical reaction.

Offline rolnor

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Re: Azidation of Tosylate
« Reply #1 on: November 02, 2019, 12:24:35 PM »
Could it bee a problem with the double bond in the ring and the azide-sidechain doing some cycloaddition?

Offline hollytara

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Re: Azidation of Tosylate
« Reply #2 on: November 04, 2019, 11:14:31 PM »
Azides and maleimides can react: Macromolecular Research, Vol. 24, No. 9,  pp 793-799 (2016)

They sell kits for creating azido PEG3 maleimide - it has to be prepared fresh as it only survives for hours after preparation - probably from reaction of azide and maleimide. 

I would very closely monitor the reaction and see if it forms and decomposes quickly.  You might also want to change the linker - for some reason 2 carbon linkers tend to give poor yields in a lot of these reactions.

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