CDMT

The use of CDMT as a coupling agent has been investigated fairly extensively, and it demonstrates several advantages over other coupling agents. It is a stable, crystalline compound, with good solubility in organic solvents, and is commercially available in large quantities.

CAS: 3140-73-6

Synonym: 2-Chloro-4,6-dimethoxy-1,3,5-triazine

Properties

Purity

≥98.0%

Molecular Formula

C5H6ClN3O2

Molecular Weight

175.57 [gr/mol]

Appearance

White to off-white crystalline powder

Storage Conditions

Store in a cool and dry place (2-8oC)

Applications

  • The standard method for making amides using CDMT is to activate the acid using CDMT and a base such as N-methylmorpholine. This generates an active ester which is subsequently reacted with the amine coupling partner in the same pot. The reaction typically proceeds to completion in a matter of 8–14 h. This method is effective for the formation of a variety of compounds, including esters and Weinreb amides. Workup of the products is typically afforded by extraction with dilute acid, as the CDMT and its triazine by-products are typically weakly basic and easily removed extractively.
  • When the product is a nonwater soluble solid, the reaction can be run in acetonitrile and many of the products isolated simply by adding water and recovering the precipitate.
  • CDMT is a reagent which has been used mainly in SPPS. In the presence of N-methylmorpholine (NMM) as base, the reagent gives low levels of racemization.
  • Numerous oligopeptides of 3-heteroaryloamino-2,3-dehydroalanine have been obtained using CDMTas the coupling reagent.
  • In the pure state CDMT is stable almost indefinitely (20 years in the author’s laboratory) without any traces of decomposition (Kamin´ ski, 1996).

Studies

  • Recent development in peptide coupling reagents
    T. I. Al-Warhi, H. M.A. Al-Hazimi, and A. El-Faham Journal of Saudi Chemical Society, 2012, 16, 97–116.
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  • A novel generation of coupling reagents. Enantiodifferentiating coupling reagents prepared in situ from 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and chiral tertiary amines
    Z. J. Kamiński, B. Kolesińska, J. E. Kamińska, and J. Góra J. Org. Chem., 2001, 66, 6276-6281.
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  • New observations on peptide bond formation using CDMT
    C. E. Garrett, X.g Jiang, K. Prasad, and O. Repic Tetrahedron Lett., 2002, 43, 4161–4165.
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