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5-Trifluoromethylfuryl derivatives of phosphocarboxylic acids

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Abstract

Methods of synthesis of trifluoromethylfuryl derivatives of phosphonocarboxylic acids are studied. By addition of diethyl hydrogen phosphite to alkyl 3-(5-trifluoromethylfur-2-yl)acrylate under the conditions of the Pudovik reaction the corresponding derivative of 3-phosphonopropionic acid was prepared. Diethyl (5-trifluoromethylfur-2-yl)methanephosphonate in presence of potassium tert-butylate reacts with ethyl acrylate to form trifluoromethylfuryl derivative of 4-phosphonobutyric or 4-phosphonopimelic acid depending on the reaction conditions. In the products of reaction of the alkyl 3-(5-trifluoromethylfur-2-yl)-3-(diethoxyphosphoryl) propionate with ethyl acrylate in the presence of potassium tert-butylate formation of trifluoromethylfuryl derivative of the 3-phosphonoadipic acid is detected. 3-(5-Trifluoromethylfur-2-yl)-3-(diethoxyphosphoryl) propionic acid and its acid chloride are synthesized. The latter compound is used for acylation of glycine to form the corresponding N-acyl derivative. It is suggested that such compounds may be transported in the cell using usual channels of transportation of the amino acids and short peptides.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    E. P. Doronina, L. M. Pevzner & M. L. Petrov

  2. Institute of Experimental Medicine, St. Petersburg, Russia

    V. A. Polukeev

Authors
  1. E. P. Doronina
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  2. L. M. Pevzner
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  3. V. A. Polukeev
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  4. M. L. Petrov
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Corresponding author

Correspondence to L. M. Pevzner.

Additional information

Original Russian Text © E.P. Doronina, L.M. Pevzner, V.A. Polukeev, M.L. Petrov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 12, pp. 1979–1986.

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Doronina, E.P., Pevzner, L.M., Polukeev, V.A. et al. 5-Trifluoromethylfuryl derivatives of phosphocarboxylic acids. Russ J Gen Chem 86, 2616–2623 (2016). https://doi.org/10.1134/S1070363216120082

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  • DOI: https://doi.org/10.1134/S1070363216120082

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