SU801513A1 - Ethyl ester of d-methyl-n-trimethylsilyl-beta-aminocrotonic acid possessing antiinflammating activity and its preparation method - Google Patents

Description

silylated amino-unsaturated carboxylic acids.

The purpose of the invention is to develop a process for the preparation of methyl methyl-N-trimethylsilyl-p-aminobutyric acid ethyl ester.

This is achieved by the proposed method for the preparation of ethyl ester with -methyl-M-trimethylsilyl-p-aminocrotonic acid;

 d-ciH-doodaHs

(iH3) -ene-1 () 5 The proposed method is simple in design and equipment and allows the use of available and non-toxic starting components, therefore, it can be recommended as a preparative one. An example. 0.1 g / zinc atom is added to a three-necked col and poured with anhydrous benzene. While stirring, a mixture consisting of ct-bromopropionic acid and adetonitrile (at 0.1 g / mol) is added dropwise. At the end of the dropping, the mixture is heated for 10-15 minutes and then trimethylporsilane is added dropwise, at the end of the dropping, the benzene is distilled off and replaced with heptane and the precipitated zinc salts are separated. PrO-Tzukt is reformed in a vacuum. Yield 49%. T. Kip. 90-92 C, | 3 mm Hg. 20 - n;.:, 1,4856 ,, d. 1.0622; MR, 1, 89. NOMA 13.0; N 6.5 Found,% s S S. Hj, Oj, MSi. calculated,%: Si 12.7; N 6 6. In the IR spectra of o1-methyl-N-trimethylsilyl-0-aminocrotonic acid ethyl ester, we observe valence vibrations of the NH group at ° 3250-3150 valence vibrations of the group at 1660-1650 cm and D (- c at 1600-1580 cm

New acid is reacted with acetonitrile in organic solvent when heated in the presence of zinc, followed by treating the resulting product with trimethylchlorosilane.

The process takes 1-2 hours.

The yield of the target product in two stages without the formation of intermediate products.

Reaction Scheme I

Nz

F -ZnBr

-dH5-c) -ci-c oo (} zH5

(dH3ij The study of the biological activity of ot-methyl-N-trimethylsilyl-0-aminocrotonic acid ethyl ester was carried out on rats of the population of W i S ta g of Stolbov nursery contained on the usual diet of the vivarium. A model of formalin inflammation was examined to evaluate the anti-inflammatory effect. Edema of the inflammatory inflammation was investigated. Edema was studied by injection plantar aponeurosis, 0.1 ml of a 2.5% formalin solution. The intensity of exudation was evaluated by measuring the volume change of the inflamed limb. Measurements were taken 3 and 6 hours after administration of phlogogen Agent. The test compound was injected with intravenously 0.5 and 3 hours after the formalin was injected at a dose of 1.5. The control group of animals received an equivalent amount of 2% starch mucus. The anti-inflammatory effect of the claimed compound was compared with the effect of amidopyrine administered intraperitoneally at a dose of 100 mg / kg. Studies have shown that ethyl ester-o1-methyl-M-trimethylsilyl-Jb-aminocrtic acid has a moderate anti-inflammatory effect. The test results are presented in the table.

Claims (3)

P given compared to control (starch mucus); Pj is given in comparison with the reference (amidopyrine). Claim 1. Inventive o1-methyl-N-trimethylsilyl-aminocrotonic acid, CI-C, C-COOCaH5 NH-5i4CH3H, which exhibits anti-inflammatory -activity. 2. A method for producing o1-methyl-M-trimethylsilyl-a-nocrotonic acid ethyl ester is concluded in that o6-bromopro-pionic acid ethyl ester is exposed to acetonitrile in an organic solvent when heated in the presence of hexane and followed by treatment with a mixture of acetonitrile and hexane; . Sources of information taken into account during the examination 1.Mashkovsky M.L. Medicines. M., Medicine, 1977, v.1, p. 182. 2.L. Blrnofer et al. MltteMung Abier SI HcoamtnosSuren und Sllarancarbonsaurecster SiПс} umha fige Aminosaurederl vate, Liebigs Ann. Chem., 1958, 22, c. 612. 3. Authors certificate of the USSR 213875, cl. From 07 F 7/10, 1967.