Acyl iodides in organic synthesis: VIII. Reactions with amino acids

Author: Voronkov M.   Belousova L.   Trukhina A.   Vlasova N.  

Publisher: MAIK Nauka/Interperiodica

ISSN: 1070-4280

Source: Russian Journal of Organic Chemistry, Vol.42, Iss.2, 2006-02, pp. : 172-174

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Abstract

Reactions of acyl iodides RCOI (R=Me, Ph) with glycine, β-alanine, and γ-aminobutyric acid were investigated. The reaction proceeded easily at room temperature without solvent involving both functional groups H2N and COOH. The prevalence of one of the reaction directions depends on the acidity of the amino acid. The more acidic glycine (pКa 2.4) reacts with RCOI affording mainly N-acylated product, whereas β-alanine (pК a 3.60) and especially γ-aminobutyric acid (pКa 4.06) are predominantly involved into exchange iodination furnishing the corresponding aminoacyl iodides.

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