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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 harsh reaction conditions, not easy to obtain, high price and the like, and achieves sufficient market supply, Mild reaction conditions and low-cost effects

Active Publication Date: 2013-03-20
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

Examples

Experimental program
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Effect test

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-oxocyclopentacarboxylate (15.6g, 0.1mol) anhydrous ethanol (155ml), stir and stir well, then cool with an ice bath To 0℃, then add sodium borohydride (2.28g, 0.06mol) in batches within 1 hour, remove the ice bath after the addition is complete, and naturally rise to room temperature, continue to stir and react for 6 hours, and then add 5% dilute hydrochloric acid (124g), the mixed solution was extracted with dichloromethane. After liquid separation, the dichloromethane layer was dried with anhydrous sodium sulfate, filtered to remove the desiccant, and the solvent was distilled off to obtain crude ethyl 2-hydroxycyclopentylcarboxylate (III). About 15.3g, the yield is about 96.8%, the crude product can be used directly in the next step without further purification.

[0034] B. Preparation of...

Embodiment 2

[0041] The other steps are the same as in Example 1, except that the preparation method of ethyl 2-hydroxycyclopentylcarboxylate (III) in step A is as follows:

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

Embodiment 3

[0044] The other steps are the same as in Example 1, except that the preparation method of ethyl 2-hydroxycyclopentylcarboxylate (III) in step A is as follows:

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

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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 chemicals, in particular to a method for preparing 1,2-cyclopentadicarboxylic acid, an intermediate of the hypoglycemic drug gliclazide. Background technique [0002] While the living standards of the people in our country are improving, the health of the people is getting more and more attention from the society. Diabetes, which is a disease of wealth, has also received more and more attention. The research on drugs used to treat such diseases is also continuing. In depth. [0003] Gliclazide, as a kind of hypoglycemic agent, has been widely used at home and abroad, and its effect is better. It is also more and more widely used in my country. However, the obsolete production process leads to higher costs, so the process is improved Reducing costs has become a new direction for research on such subjects. [0004] For the preparation of gliclazide's key intermediate compound 1,2-cyclopentadicarboxylic acid, the existin...

Claims

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Application Information

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