DERIVATIVES OF 5-AMINOISOXAZOL - CONFORMATIONALLY-RIGID ANALOGS OF G-AMINO BUTYRIC ACID AND ITS PRODUCTION METHOD Russian patent published in 2017 - IPC C07D261/14 C07F9/653 

FIELD: chemistry.

SUBSTANCE: invention relates to 5-aminoisoxazole-3-phosphonic acid of the general formula 1 , which is the conformationally rigid analog of γ-aminobutyric acid (GABA). The production process of 5-aminoisoxazole-3-phosphonic acid is carried out by adding to the diethyl ether the vinylphosphonic acid of 1.5-2.5-times excess of diisopropylethylamine and a 1.5-3-times excess of tetranitromethane. Then the resulting nitroethers reduce the non-destructive isoxazole fragment with the chemoselective system, containing 2-20 times with respect to the nitroether the reducing agent excess, followed by the hydrolysis of the resulting amino ethers. 30-40 wt % of zinc suspension in acetic acid, containing 5-15-times excess of zinc, relative to the nitro ether is used as the chemoselective system. Also as the chemoselective system, use 30-50 wt % of tin chloride (II) solution in 96% by volume aqueous ethanol, containing 5-20-times excess of tin chloride (II) with respect to the nitroether, or use 2-10 wt % of sodium dithionite solution in 30-70 vol % aqueous methanol, containing 2-10-times excess of sodium dithionite with respect to the nitric ether. The hydrolysis of the amino ethers is carried out with 3-10-fold excess of trimethylsilyl iodide, followed by treatment of the resulting mixture with 75 vol % solution of propylene oxide in methanol, containing 20-40-times excess of propylene oxide with respect to the amino ether.

EFFECT: above mentioned acid, which is the conformationally rigid analog γ-aminobutyric acid.

6 cl, 4 ex