Bulky Base Works Well for Deprotonation

M.D. Anderson

Overall

Quality of Results

Ease-of-Optimization

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Company:

Sigma-Aldrich

Product Name:

Triethylamine

Catalog Number:

471283

Synthesis of new peptide bond starting from an acyl chloride and an amide in a dry atmosphere of N2, using bulky base.

Experimental Design and Results Summary

Application

Deprotonation

Starting Material

2HN-PEG-N3

Tips

Use lab gloves due to bad smell of the product.

Results Summary

The triethylamine, since is a bulky base, is useful to deprotonate compounds without being aware of it possible reactivity as a nucleophile.

DOI or PMID #

None

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Summary

The Good

Work well and doesn't act as nucleophile.

The Bad

Bad smell and be aware of any drops on the skin.

The Bottom Line

I use the triethylamine as bulky base for deprotonation in the synthesis of new peptide bond. I used 2.1 equivalent to push the reaction on the right side and so be sure that all the intermediate, form from the reaction between the acyl chloride and the amine, would have been deprotonate.

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