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All posts Subject: Solvents For Amide Synthesis Please login to post

Bubbleplate
(Hive Bee)
10-10-04 16:26
No 535200
Solvents For Amide Synthesis

Most of the procedures for the "Carbonyldiimidazole" reaction to produce LSD specify DimethylFormamide (DMF) as the solvent to run it in.
A few articles I've run across regarding Peptide Coupling Agents, (for instance http://www.peptide-and-dna.com/marder.pdf )
it is suggested that Choloroform or DCM may be better solvents to carry out the reaction in. The above article says "If the activation is carried out in a solvent of low dielectric constant such as CHCl3 or CH2Cl2, the formation of {the carbodiimide} occurs instaneously...... However, if the activation is carried out in a more Polar solvent such as DMF, no immediate reaction can be detected and a complex mixture..."
My question is, while the article is about Peptide coupling, would this also be applicable to the Lysergic Acid/N,N-Carbonyldiimidazole reaction?
Also, in general, does using solvents of low dielectric constant, like DCM or Choloform, have any potential downside ?

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	All posts		Subject: Solvents For Amide Synthesis		Please login to post


		Bubbleplate (Hive Bee) 10-10-04 16:26 No 535200				Solvents For Amide Synthesis
						Most of the procedures for the "Carbonyldiimidazole" reaction to produce LSD specify DimethylFormamide (DMF) as the solvent to run it in. A few articles I've run across regarding Peptide Coupling Agents, (for instance http://www.peptide-and-dna.com/marder.pdf ) it is suggested that Choloroform or DCM may be better solvents to carry out the reaction in. The above article says "If the activation is carried out in a solvent of low dielectric constant such as CHCl3 or CH2Cl2, the formation of {the carbodiimide} occurs instaneously...... However, if the activation is carried out in a more Polar solvent such as DMF, no immediate reaction can be detected and a complex mixture..." My question is, while the article is about Peptide coupling, would this also be applicable to the Lysergic Acid/N,N-Carbonyldiimidazole reaction? Also, in general, does using solvents of low dielectric constant, like DCM or Choloform, have any potential downside ?

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