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Method for preparing intermediate 1,2-dicarboxylicacid of antidiabetic medicine gliclazide

A technology of cyclopentanedicarboxylic acid and ethyl cyclopentamate, which is applied in the field of hypoglycemic drug gliclazide intermediate 1, can solve the problems of difficult availability, harsh reaction conditions, high temperature and long time reaction, etc., and achieves the reaction conditions Moderate, sufficient market supply, cost reduction effect

Active Publication Date: 2011-02-02
ANHUI JINDING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction conditions of each step of the method are harsh, especially the rearrangement step requires high temperature and long-term reaction, which consumes a lot of energy, and the by-products produced are not easy to remove, the yield is not high, and it cannot meet the requirements of green and sustainable development.
[0005] In addition, literature (Tetrahedron: Asymmetry Vol 17, (2006), 107-111), literature (J.Am.Chem.Soc., 2005, 127 (2), 514515) also reports that other methods prepare target compound, but The raw materials used are relatively special, expensive and difficult to obtain, and industrial production cannot be realized

Method used

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  • Method for preparing intermediate 1,2-dicarboxylicacid of antidiabetic medicine gliclazide
  • Method for preparing intermediate 1,2-dicarboxylicacid of antidiabetic medicine gliclazide

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Embodiment 1

[0032] A. Preparation of ethyl 2-hydroxycyclopentylcarboxylate (III)

[0033] In a reactor equipped with a mechanical stirring device, a reflux condenser, and a mercury thermometer, add ethyl 2-oxocyclopentanoate (15.6g, 0.1mol) absolute ethanol (155ml), stir and cool with an ice bath to 0°C, and then add sodium borohydride (2.28g, 0.06mol) in batches within 1 hour. After the addition, remove the ice bath, naturally rise to room temperature, and continue stirring for 6 hours. After the reaction is complete, add 5% dilute hydrochloric acid (124g), the mixed solution is extracted with dichloromethane again, and the dichloromethane layer is dried with anhydrous sodium sulfate after the liquid separation, and after the desiccant is removed by filtration, the solvent is distilled off to obtain the crude product of ethyl 2-hydroxycyclopentylcarboxylate (III), About 15.3g, the yield is about 96.8%, the crude product can be directly used in the next reaction without further purificati...

Embodiment 2

[0041] Other steps are identical with embodiment 1, just the preparation method of the 2-hydroxycyclopentyl ethyl carboxylate (III) of A step is as follows:

[0042] In a reactor equipped with a mechanical stirring device, a reflux condenser, and a mercury thermometer, add ethyl 2-oxocyclopentanoate (15.6g, 0.1mol) absolute ethanol (100ml), stir and cool with an ice bath to 0°C, then add sodium borohydride (1.9 g, 0.05 mol) in batches within 1 hour, remove the ice bath after the addition, naturally rise to room temperature, continue stirring for 4 hours, and then add 5% dilute hydrochloric acid (78g), the mixed solution is extracted with dichloromethane again, and the dichloromethane layer is dried with anhydrous sodium sulfate after the liquid separation, and after the desiccant is removed by filtration, the solvent is distilled off to obtain the crude product of ethyl 2-hydroxycyclopentylcarboxylate (III), About 14.1 g, the yield is about 89.2%, the crude product can be dire...

Embodiment 3

[0044] Other steps are identical with embodiment 1, just the preparation method of the 2-hydroxycyclopentyl ethyl carboxylate (III) of A step is as follows:

[0045] In a reactor equipped with a mechanical stirring device, a reflux condenser, and a mercury thermometer, add ethyl 2-oxocyclopentanoate (15.6g, 0.1mol) anhydrous methanol (155ml), stir and cool with an ice bath to 0°C, and then add potassium borohydride (3.24g, 0.06mol) in batches within 1 hour, remove the ice bath after the addition, naturally rise to room temperature, continue to stir and react for 6 hours, and then add 5% dilute hydrochloric acid (124g), the mixed solution is extracted with dichloromethane again, and the dichloromethane layer is dried with anhydrous sodium sulfate after the liquid separation, and after the desiccant is removed by filtration, the solvent is distilled off to obtain the crude product of ethyl 2-hydroxycyclopentylcarboxylate (III), About 15 g, the yield is about 94.9%, the crude pro...

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Abstract

The invention discloses a method for preparing intermediate 1,2-dicarboxylicacid of an antidiabetic medicine gliclazide. The method comprises the steps of reducing, eliminating, adding and hydrolyzing 2-oxocyclopentanecarboxylate serving as a raw material to prepare the product. The invention provides a brand-new synthesis route, and has the advantages wide and rich sources and low price of the raw material, mild reaction condition and simple process; and reactions in each step are conventional operation, so the production cost is reduced.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a method for preparing a hypoglycemic drug gliclazide intermediate 1,2-cyclopentadicarboxylic acid. Background technique [0002] While the living standards of the people in our country are improving day by day, the health of the people is getting more and more attention from the society, and diabetes, which is a disease of the rich and the rich, is getting more and more attention. in-depth. [0003] Gliclazide, as a kind of hypoglycemic drug, has been widely used at home and abroad, and the effect is better. It is also more and more widely used in our country, but the obsolete production process leads to high cost, so the improvement process Cost reduction has become a new direction of research on this type of subject. [0004] For the preparation of the key intermediate compound 1,2-cyclopentadicarboxylic acid of gliclazide, the existing process generally uses cyclohexan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C27/02C07C61/06C07C51/08
Inventor 向太平蒋爱萍
Owner ANHUI JINDING PHARMA
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