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Method for removing residual palladium in crude product of faropenem sodium prepared by palladium catalysis method

A technology catalyzed by faropenem sodium and palladium, which is applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problems of high industrial production costs and low product yields, etc. problems, to achieve the effect of simple operation, solving technical problems, and good adsorption effect

Inactive Publication Date: 2009-11-11
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, after multiple recrystallizations, the yield of the product is greatly reduced, which leads to problems such as high industrial production costs.

Method used

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  • Method for removing residual palladium in crude product of faropenem sodium prepared by palladium catalysis method
  • Method for removing residual palladium in crude product of faropenem sodium prepared by palladium catalysis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A palladium catalyzed preparation of crude faropenem sodium (I):

[0025] Put sodium isooctanoate (4.33g, 0.026mol) and deionized water (3.4mL) in the reaction flask and stir until dissolved, then add (1′R, 2″R, 5R, 6S)-6-[(1′ -Hydroxyethyl)-2"-tetrahydrofuryl]penicillene-3-carboxylic acid allyl ester (8.5g, 0.026mol) and ethyl acetate (34mL) solution, and replace the air in the reaction flask with nitrogen and quickly add Tetrakis(triphenylphosphine)palladium (0.3g, 0.26mmol) and triphenylphosphine (0.34g, 1.3mmol), after stirring at 25°C for 5 hours, cooling to 0°C and stirring for 0.5 hours, filtering, filter cake After washing with ethyl acetate, the crude faropenem sodium (I) was obtained. The crude product was detected by ICP emission spectrometer and the palladium content was 68 ppm.

[0026] B. Removal of residual palladium:

[0027] The crude faropenem sodium (I) (palladium content 0.578mmol) was prepared into a saturated aqueous solution (24.5mL) with deionized wa...

Embodiment 2

[0029] A palladium catalyzed preparation of crude faropenem sodium (I):

[0030] Place sodium bicarbonate (5.2g, 61.4mmol) and deionized water (8mL) in a reaction flask, stir and add 5,5-dimethylcyclohexanedione (5.2g, 37.2mmol) in batches, and wait until the addition is complete. Then continue to stir until the reaction solution is clear, and then add (1′R,2″R,5R,6S)-6-[(1′-hydroxyethyl)-2″-tetrahydrofuryl]penem-3-carboxylic acid After a solution of allyl ester (20g, 61.4mmol) and ethyl acetate (80mL), and replacing the air in the reaction flask with nitrogen, bis(triphenylphosphine)palladium dichloride (1.0g, 1.43mmol) was quickly added to After stirring for 5 hours at 25°C, then cooling to 0°C and stirring for 0.5 hours, filtering, and washing the filter cake with ethyl acetate, it is the crude faropenem sodium (I). The crude product was detected by ICP emission spectrometer and the palladium content was 104ppm.

[0031] B. Removal of residual palladium:

[0032] The crude faro...

Embodiment 3

[0034] A palladium catalyzed preparation of crude faropenem sodium (I):

[0035]Place sodium bicarbonate (5.2g, 61.4mmol) and deionized water (8mL) in a reaction flask, stir and add 5,5-dimethylcyclohexanedione (5.2g, 37.2mmol) in batches, and wait until the addition is complete. Then continue to stir until the reaction solution is clear; then add (1′R,2″R,5R,6S)-6-[(1′-hydroxyethyl)-2″-tetrahydrofuryl]penem-3-carboxylic acid After a solution of allyl ester (20g, 61.4mmol) and acetone (80mL), and replacing the air in the reaction flask with nitrogen, quickly add palladium dichloride (0.25g, 1.43mmol) and triphenylphosphine (0.674g, 2.57mmol) ). After stirring at 25°C for 5 hours, then cooling to 0°C and stirring for 0.5 hours, filtering, and washing the filter cake with ethyl acetate, it is the crude faropenem sodium (I). This crude product is detected by ICP emission spectrometer. The content of palladium is It is 200ppm.

[0036] B. Removal of residual palladium:

[0037] The cr...

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Abstract

The invention relates to a method for removing residual palladium in crude product of faropenem sodium prepared by a palladium catalysis method, belonging to the field of organic medicinal chemistry. The method comprises the following steps of: preparing the crude product of faropenem sodium with residual palladium content being 20-200ppm into saturated solution by deionized water; adding thiocyanuric acid loaded by polystyrene, and then mixing and stirring; filtering the mixed liquor; adding acetone into the filtrate slowly during the stirring process; and precipitating the faropenem sodium with the residual palladium content under 110ppm, wherein the molar ratio of the residual palladium in the crude product of faropenem sodium to the thiocyanuric acid in the thiocyanuric acid loaded by polystyrene is 1:1-10, and the volume ratio of the saturated solution of the crude product of faropenem sodium to the acetone is 1:1-50. The method has easily-obtained raw materials, is low in cost and good in absorbing effect, is suitable for removing the residual heavy metal palladium in the crude product of faropenem sodium by the thiocyanuric acid loaded by polystyrene in industrial production, has simple and convenient operation and good removing effect, and leads the faropenem sodium product to meet pharmacopoeia requirements.

Description

Technical field [0001] The invention belongs to the field of organic pharmaceutical chemistry, and relates to a method for removing residual palladium from crude faropenem sodium prepared by a palladium (0 or II) catalytic method. Background technique [0002] Faropenem sodium is a penicillene antibiotic developed by Japan's Suntory Company. It was first listed in Japan in 1997. The drug has the characteristics of wide antibacterial spectrum, strong antibacterial activity, and stability to β-lactam mold. At the same time, it can be taken orally and injected, and effectively inhibits Gram-positive, negative bacteria and anaerobic bacteria. Its chemical name: (5R, 6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-2-tetrahydrofuranyl]-4-thio-1- Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt, which is usually a hydrate with 2.5 water molecules. The structural formula of faropenem sodium is: [0003] [0004] Existing literature ① EP199446, literature ② (Han Hongna et al. Chinese...

Claims

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Application Information

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IPC IPC(8): C07D499/893C07D499/18B01J31/24B01J27/10A61P31/04
Inventor 陈芬儿黄建平赵磊古双喜
Owner FUDAN UNIV
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