What are Better Coupling Reagents for Reacting an Amine with a Carboxylic Acid?

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Discussion Overview

The discussion revolves around identifying effective coupling reagents for the reaction between an amine and a carboxylic acid. The focus is on exploring alternatives to TBTU, which the original poster finds ineffective in their specific reaction setup.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • The original poster is using TBTU with fenchyl amine hydrochloride but is experiencing issues with the reaction not proceeding as expected.
  • One participant provides a list of alternative coupling reagents, including CDI, HOBT, DCC, and EDCI, suggesting they are commonly used.
  • A link to a resource with additional coupling reagents and their CAS numbers is shared for further reference.
  • Another participant expresses interest in the chemistry discussion but does not contribute specific technical insights.

Areas of Agreement / Disagreement

There is no consensus on the best coupling reagent, as the original poster is seeking alternatives while others provide suggestions without confirming their effectiveness in this specific context.

Contextual Notes

The discussion does not address the specific conditions or limitations of the reactions being attempted, such as solvent choice, temperature, or concentration, which may influence the effectiveness of the coupling reagents.

Who May Find This Useful

Chemists, researchers, and students interested in organic synthesis and coupling reactions may find this discussion relevant.

gravenewworld
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I'm trying to find a coupling reagent for reacting an amine with a carboxylic acid. Currently I am using TBTU with fenchyl amine hydrochloride, but the amine seems not to want to react witht the carboxylic acid. Are there some better coupling reagents than TBTU out there that anyone knows of?
 
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Here's a whole list of them:

http://www.glschina.com/en/pro/peppro/cou.htm

They've got the CAS numbers listed there so you can cross-reference them to a chemical catalog.

I would say the ones I have seen the most often are CDI, HOBT, DCC, and EDCI.
 
awesome thanks!
 
I don't have anything to contribute to this thread, however you two dudes seem into this whole chemistry game.

Perhaps you'd be interested in the following forum:

http://www.sciencemadness.org/talk/
 

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