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Topic: neutralizing HCl salt from EDC-HCl for amide coupling ?  (Read 3248 times)

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Offline metallocene2015

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neutralizing HCl salt from EDC-HCl for amide coupling ?
« on: January 17, 2015, 01:19:35 AM »
Hi everyone, 

 I am currently doing an amide coupling reaction between naphthyridine dicarboxylic acid and 2-aminomethylpyridine using EDC-HCl, DMAP,HOBt, DMF- for those of you who have used EDC before, did you add base to neutralize the HCl salt before/during/after the reaction or is it not necessary ? I am worried that the acidic conditions will protonate my starting materials and cause problems during workup.

Offline TheUnassuming

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Re: neutralizing HCl salt from EDC-HCl for amide coupling ?
« Reply #1 on: January 26, 2015, 03:02:37 PM »
I usually just add straight DI water and extract.  The high water solubility of EDCI is the major advantage/reason for using it over other carbodiimides.  So if you leave the EDC/urea product protonated it will stay in the aqueous layer and make purification much easier.   
When in doubt, avoid the Stille coupling.

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