Synthesis of trifluoromethyl derivatives of alkyl 2-nitromethylphosphonopropionates and -phosphonobutyrates
- Authors: Doronina E.P.1, Pevzner L.M.1, Polukeev V.A.2, Petrov M.L.1
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Affiliations:
- St. Petersburg State Institute of Technology (Technical University)
- Institute of Experimental Medicine
- Issue: Vol 87, No 3 (2017)
- Pages: 447-455
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/218714
- DOI: https://doi.org/10.1134/S1070363217030136
- ID: 218714
Cite item
Abstract
By adding diethyl hydrogen phosphite to 5-trifluoromethyl-2-furaldehyde (5-trifluoromethylfur-2-yl)(diethoxyphosphoryl)methanol was synthesized. It was oxidized with DMSO-acetic anhydride mixture to diethyl 5-trifluoromethyl-2-furoyl phosphonate. The reaction of the latter with ethoxymethylenetriphenylphosphorane gives ethyl (2E)-3-(diethoxyphosphoryl)-3-(5-trifluoromethylfur-2-yl)propenoate. Analogous reaction of (diethoxyphosphoryl)(5-trifluoromethylfur-2-yl)acetic aldehyde yields ethyl (4E)-4-(diethoxyphosphoryl)-4-(5-trifluoromethylfur-2-yl)-but-3-enoate. The addition of nitromethane to these esters of unsaturated acids in the presence of potassium fluoride gives a mixture of diastereomers of phosphorylated esters of 2-nitromethyl-3-(5-trifluoromethylfur-2-yl)propanoic and 3-nitromethyl-4-(5-trifluoromethylfur-2-yl)butanoic acids respectively. By the reduction of ethyl nitropropanoate with zinc and formic acid in dioxane ethyl 2-aminomethyl-3-(diethoxyphosphoryl)-3-(5-trifluoromethylfur-2-yl)propanoate was prepared in a low yield. It may be considered as the derivative of β-alanine containing additional pharmacophore fragments.
About the authors
E. P. Doronina
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
L. M. Pevzner
St. Petersburg State Institute of Technology (Technical University)
Author for correspondence.
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
V. A. Polukeev
Institute of Experimental Medicine
Email: pevzner_lm@list.ru
Russian Federation, St. Petersburg
M. L. Petrov
St. Petersburg State Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
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