[vivioo7]

Im planning to use EDC to catalyze the reaction of a carboxylic acid and an amine in water solution.  I will use a neutral salt of the acid, at STP, and pH 7.2, does all of this sound right to you guys?  Thanks for the help 

Sorry to be posting about this again so soon but the water solution part is a necessity and I havent found any relevant articles.  If you want to share how to search for this answer Id appreciate that also.   

[cpncoop]

Hi,

I think I'd need to know more about the reaction but EDC isn't typically used as a catalyst.  It is used in stoichiometric amounts in order to form the active ester of the carboxylic acid, which then undergoes attack by the amine.  Also, running the reaction in water can be problematic since the active ester typically will react with the water.  I'd run this reaction in dry DCM or DMF.

[orgopete]

You should consult a book on peptide chemistry. That should give you a range of conditions that you may find compatible. It would seem that you can hypothetically run your reaction is water. An amine is more nucleophilic than water, but this is going to be a rate effect. If the amine if much faster, okay, but if it is slow, then more hydrolysis. A Schotten-Baumann reaction is typically run in water to form amides.

[cpncoop]

Excellent point on Schotten-Baumann conditions... The technique is a personal favorite - can't believe I didn't think of it....