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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: metallocene2015 on January 17, 2015, 01:19:35 AM

Title: neutralizing HCl salt from EDC-HCl for amide coupling ?
Post by: metallocene2015 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.

Title: Re: neutralizing HCl salt from EDC-HCl for amide coupling ?
Post by: TheUnassuming 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.