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Preparation method of gefarnate

A technology of gefidate and ethyl acetate, applied in the field of pharmaceutical synthesis, can solve the problems of long synthesis route of gemfidate, unsuitable for industrial production, complicated post-processing, etc., achieves less solvent residue, improved reaction conversion rate, and avoids polymerization effect of reaction

Active Publication Date: 2013-04-03
广东暨大基因药物工程研究中心有限公司
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  • Summary
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The purpose of the present invention is to provide a synthetic method of gefar esters, to solve the technical problems of long synthesis route, low yield, low yield purity, complex post-treatment and inapplicability to industrialized production in the prior art.

Method used

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  • Preparation method of gefarnate

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preparation example Construction

[0047] One invention of the present invention provides a kind of preparation method of gefar ester, comprises the following steps:

[0048] 1) Phosphorylation of ethyl bromobutyrate to obtain phosphorus ylide solution, and Wittig reaction of phosphorus ylide solution with geranyl acetone to obtain ethyl farnesyl acetate;

[0049] 2) adding sodium hydroxide and N,N-dimethylformamide to ethyl farnesyl acetate for acidification reaction to obtain farnesyl acetic acid;

[0050] 3) Add geraniol, xylene, and a polymerization inhibitor to farnesyl acetic acid, carry out the steps of heating to reflux, and concentrating under reduced pressure, and collect and fractionate at 186-200°C to obtain gefar esters.

[0051] The present invention carries out Wittig reaction with phosphorus ylide solution and geranyl acetone to obtain ethyl farnesyl acetate, and its reaction equation is The Wittig reaction conditions are mild, and the reaction can be performed at room temperature, and the yie...

Embodiment 1

[0067] 1) Dissolve 182g of ethyl 4-bromobutyrate in 600ml of tetrahydrofuran in a 1000mL three-necked flask, add 242.8g of triphenylphosphine, add 182g of triethylamine, stir at room temperature for 5 hours, distill off the tetrahydrofuran solution , the resulting phosphorus ylide solution. Dissolving 190 g of geranyl acetone in 800 ml of dichloromethane to obtain a geranyl acetone solution, mixing the geranyl acetone and phosphorus ylide solution, stirring and reacting at room temperature for 2-3 hours to obtain a reaction liquid. The reaction solution was distilled to remove dichloromethane, and the by-product triphenylphosphine oxide generated by the reaction was removed by alcohol recrystallization from the residue to obtain solution 1. After the solution is filtered, the filtrate is concentrated until there is no alcohol smell, dissolved in ethyl acetate, washed once with 800ml of water, and then washed once with 500ml of saturated saline to obtain an organic phase, and t...

Embodiment 2

[0072] 1) Dissolve 195g of ethyl 4-bromobutyrate in 600ml of tetrahydrofuran in a 1000mL three-necked flask, add 262g of triphenylphosphine, add 150g of triethylamine and stir at room temperature for 5 hours, distill off the tetrahydrofuran solution, The resulting phosphorus ylide solution. Dissolving 190 g of geranyl acetone in 800 ml of dichloromethane to obtain a geranyl acetone solution, mixing the geranyl acetone and phosphorus ylide solution, stirring and reacting at room temperature for 2-3 hours to obtain a reaction liquid. The reaction solution was distilled to remove dichloromethane, and the by-product triphenylphosphine oxide generated by the reaction was removed by alcohol recrystallization from the residue to obtain solution 1. After the solution is filtered, the filtrate is concentrated until there is no alcohol smell, dissolved in ethyl acetate, washed once with 800ml of water, and then washed once with 500ml of saturated saline to obtain an organic phase, and t...

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Abstract

The invention provides a preparation method of gefarnate. The preparation method is characterized by comprising the following steps: conducting phosphorylation reaction on bromobutyric acid ethyl ester and triphenylphosphine to obtain phosphorus ylide solution, conducting whittig reaction to the phosphorus ylide solution and geranylacetone to obtain farnesyl ethyl acetate; adding the farnesyl ethyl acetate into sodium hydroxide and N,N-dimethylformamide so as to conduct acidification reaction to obtain farnesyl acetic acid; and adding geraniol, dimethylbenzene and a polymerization inhibitor into farnesyl acetic acid for conducting heating reflux and vacuum concentration, and collecting fraction at 186-200 DEG C to obtain gefarnate. According to the method, the technical problems that the gefarnate obtained in the prior art is long in synthetic route, low in yield, low in yield purity, complicated in after-treatment, and not applicable to industrial production can be solved.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of gefarate. Background technique [0002] Gefate is an isoprene compound, which has the functions of accelerating metabolism, regulating gastrointestinal function and gastric acid secretion, and strengthening mucosal protection. The mechanism of action may be to act directly on gastric mucosal epithelial cells to enhance their ability to resist ulcerative factors. For the treatment of gastric and duodenal ulcers, acute and chronic gastritis, colitis, gastric disease, etc. At present, there is no Jifa vinegar raw material on the market in China. Jifa enzyme is initially isolated from cabbage, and then synthesized by Adami and others. It is marketed by Nippon Shengko Rongyang Pharmaceutical Co., Ltd. Since its launch, it has treated innumerable patients with gastrointestinal diseases, and has been highly praised by the international medical community, and patie...

Claims

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Application Information

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IPC IPC(8): C07C69/587C07C67/08
Inventor 张庆华孙先仁
Owner 广东暨大基因药物工程研究中心有限公司
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