How can I attach an amine group (-NH2) to a carboxyl group (-COOH)? What are the experimental conditions, such as temperature, atmosphere, pH etc? I want to attach mPEG-NH2 to α-Lipoic acid in water solutions.
Cant do the reaction in water.
You can use HATU + triethylamine + DMF or DCM solvent
you want an amid right? try conditions a la steglich esterification..it works for amines, too.
coupling reagent would be DCC for example
Greg Petruncio
Thank you for your help. Why can't I do this reaction in water? please tell me further details.
When you make your active ester (turns the carboxylic acid OH into a good leaving group) a nucleophile can come in and attack carbonyl carbon. This nucleophile can be RNH2, ROH, or—in unwanted cases— H2O which simply regenerates your starting carboxylic acid.
Dissolve the acid in DMF add DCC then add ammonium formate or acetate. Remove solvent, work up. You get the corresponding amide. Good luck!
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