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

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SUMMARY

The discussion focuses on identifying superior coupling reagents for the reaction between amines and carboxylic acids. The user currently employs TBTU with fenchyl amine hydrochloride but reports a lack of reactivity. Recommended alternatives include CDI, HOBT, DCC, and EDCI, which are frequently cited in the literature. A resource listing various coupling reagents along with their CAS numbers is provided for further reference.

PREREQUISITES
  • Understanding of amine and carboxylic acid chemistry
  • Familiarity with coupling reagents such as TBTU, CDI, HOBT, DCC, and EDCI
  • Knowledge of chemical reaction mechanisms
  • Access to chemical catalogs for cross-referencing CAS numbers
NEXT STEPS
  • Research the mechanisms of action for CDI and HOBT as coupling reagents
  • Explore the advantages and limitations of DCC and EDCI in peptide synthesis
  • Investigate alternative coupling reagents listed on the provided GLS China resource
  • Review literature on optimizing amine and carboxylic acid reactions
USEFUL FOR

Chemists, researchers in organic synthesis, and anyone involved in peptide synthesis or coupling reactions will benefit from this discussion.

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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