New preparation method for gefarnate key intermediate

A technology of gefar esters and intermediates, which is applied in the preparation of carboxylic acid esters, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems that are not suitable for industrial production, achieve simple operation, mild reaction conditions, and reduce energy consumption Effect

Inactive Publication Date: 2012-04-04
NANJING REAL PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] Patent CN101805260A improves on this basis, uses triethyl orthoacetate and uses ethanol as solvent, this method has avoided using methanol, but used ether in this route, and the purification of intermediate and product all used column chromatography, not Suitable for industrial production

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  • New preparation method for gefarnate key intermediate
  • New preparation method for gefarnate key intermediate
  • New preparation method for gefarnate key intermediate

Examples

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Embodiment 1

[0047]Add 110g of intermediate (III) into a 1000ml three-neck flask, add 202g of potassium carbonate, 1.6g of sodium iodide, 76g of diethyl malonate, and 200ml of acetone, and heat up to reflux reaction (internal temperature 60-70°C), TLC Track the completion of the reaction (developing agent: ethyl acetate:petroleum ether=1:9; iodine color development) for about 4 hours. After the reaction is complete, acetone is recovered under normal pressure, and 200ml of purified water is added to the reaction bottle and stirred until the potassium carbonate is dissolved, and the water is separated. Layer, collect the organic layer, combine the organic layer, dry with anhydrous sodium sulfate, filter with suction, remove the fraction before 100°C from the organic layer under reduced pressure, and the residue is intermediate (IV) 146.3g.

[0042] Gefarate purity inspection method: high performance liquid chromatography-evaporative light scattering detection (HPLC-ELSD) method, chromatograph...

Embodiment 2

Embodiment 3

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Abstract

The invention discloses a new preparation method for a gefarnate key intermediate (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecyl triolefinic acid, and belongs to medicines. The method comprises the following steps of: reacting nerolidol with hydrogen chloride to obtain an intermediate (III) and then condensing with diethyl malonate to obtain an intermediate (IV); then hydrolyzing and acidifying to obtain an intermediate (V); and finally removing a carboxylic acid to obtain the gefarnate key intermediate. In the preparation method, methanol with high toxicity and combustible and explosive diethyl ether used in the prior art are effectively avoided in a production process, and the safety is enhanced; and the method has the advantages of mild reaction conditions, easiness and convenience in operation and high suitability for industrial production. The prepared gefarnate key intermediate is not required to be purified and can be directly prepared into the gefarnate with geraniol through a method well known by those of skill in the art; and the purity can reach over 99.5 percent.

Description

technical field [0001] The present invention relates to a preparation method of formula (I) compound (4E, 8E)-5,9,13-trimethyl-4,8,12-tetratrienoic acid, which is used for the preparation of gastric mucosa protective drug gefarate The key intermediate belongs to the field of medicine. [0002] Background technique [0003] The chemical name of Gefarnate is (4E, 8E)-5,9,13-trimethyl-4,8,12-tetratrienoic acid-(2E)-3,7-dimethyl-2 , 6-octadienyl ester, its chemical structural formula is shown in the following formula. [0004] [0005] Gefate [0006] Gefate is an isoprene compound, which was originally extracted from cabbage heart and then synthesized by Adami et al. For the treatment of gastric and duodenal ulcers, acute and chronic gastritis, colitis, stomach cramps, etc. It has the effects of accelerating metabolism, regulating gastrointestinal function and gastric acid secretion, and strengthening mucosal protection. The mechanism of action may be to act direct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/03C07C51/38C07C69/587C07C67/08
Inventor 时文祥于居超叶靖相文杰
Owner NANJING REAL PHARMA
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