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Method for removing residual palladium of faropenem sodium

A technology of faropenem sodium and removal method, which is applied in the field of medicinal chemistry, can solve problems such as palladium residues and the like, and achieves the effects of simple operation, easy availability of raw materials and good adsorption effect.

Inactive Publication Date: 2009-10-21
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The serious defect of above-mentioned method is: the use of palladium (zero valence or divalent) catalyst all will have caused the residue of heavy metal palladium in the crude product of faropenem sodium, and its residue is 200~2000ppm

Method used

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  • Method for removing residual palladium of faropenem sodium
  • Method for removing residual palladium of faropenem sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Sodium isooctanoate (4.33g, 0.026mol) and deionized water (3.4mL) were placed in a reaction flask and stirred until dissolved, then (1′R, 2″R, 5R, 6S)-6-[(1 '-Hydroxyethyl)-2"-tetrahydrofuryl] penem-3-carboxylic acid allyl ester (8.5g, 0.026mol) and ethyl acetate (34mL) solution, and after replacing the air in the reaction flask with nitrogen, Tetrakis(triphenylphosphine)palladium (0.3 g, 0.26 mmol) and triphenylphosphine (0.34 g, 1.3 mmol) were added rapidly. After stirring at 25°C for 5 hours, cool to 0°C and continue to stir for 0.5 hours, filter, and wash the filter cake with ethyl acetate to obtain the crude product of faropenem sodium (I). The crude product is detected by an ICP emission spectrometer, and the palladium content is 1068ppm. Then dissolve the crude product of faropenem sodium (I) in 85 mL of methanol, add 767 injections of activated carbon (0.1 g), stir at 25 °C for 12 h, filter with Buchner funnel, spin dry the alcohol solvent in the filtrate at 25...

Embodiment 2

[0021] After sodium bicarbonate (5.2g, 61.4mmol) and deionized water (8mL) were placed in the reaction flask and stirred and dissolved, 5,5-dimethylcyclohexanedione (5.2g, 37.2mmol) was added in batches and waited Continue to stir until the reaction solution is clear after the addition; Allyl carboxylate (20g, 61.4mmol) and ethyl acetate (80mL) solution, and after replacing the air in the reaction flask with nitrogen, quickly add two (triphenylphosphine) palladium dichloride (1.0g, 1.43mmol) . Stir at 25°C for 5 hours, then cool to 0°C and continue stirring for 0.5 hours, filter, and wash the filter cake with ethyl acetate to obtain the crude product of faropenem sodium (I). The crude product is detected by ICP emission spectrometer, and the palladium content It is 1004ppm. Then dissolve the crude product of faropenem sodium (I) in 200 mL of methanol, add 767 injections of activated carbon (0.24 g), stir at 25 ° C for 12 h, filter it with a Buchner funnel, and spin dry the a...

Embodiment 3

[0023] After sodium bicarbonate (5.2g, 61.4mmol) and deionized water (8mL) were placed in the reaction flask and stirred and dissolved, 5,5-dimethylcyclohexanedione (5.2g, 37.2mmol) was added in batches and waited Continue to stir until the reaction solution is clear after the addition; Allyl carboxylate (20g, 61.4mmol) and acetone (80mL) solution, and after the air in the reaction flask was replaced with nitrogen, palladium dichloride (0.25g, 1.43mmol) and triphenylphosphine (0.674g, 2.57 mmol). Stir at 25°C for 5 hours, then cool to 0°C and continue stirring for 0.5 hours, filter, and wash the filter cake with ethyl acetate to obtain the crude product of faropenem sodium (I). The crude product is detected by ICP emission spectrometer, and the palladium content 2000ppm. Then the crude product was dissolved with 200mL of methanol, 767 injection of activated carbon (0.24g) was added, and after stirring for 12h at 25°C, it was suction-filtered with a Buchner funnel, and the al...

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Abstract

The invention belongs to the field of medicinal chemistry, and in particular relates to a method for removing residual palladium with high content of a faropenem sodium crude product. The method comprises the following steps: stirring and adsorbing an alcoholic solution or an aqueous solution of the faropenem sodium crude product with the palladium content of 200 to 2,000 ppm and active carbon for 5 minutes to 48 hours at a temperature of between 0 and 45 DEG C; decompressing a filtered filtrate to reclaim the alcoholic solvent; dissolving remnant with deionized water or directly adding an organic solvent dropwise to the filtrate obtaining by filtering the aqueous solution of the faropenem sodium crude product; and precipitating a faropenem sodium hydrate with the palladium residual quantity of below 10 ppm. The method has simple and convenient operation, low cost and good palladium removing effect, and is suitable to be used in the industry.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a method for removing residual palladium of faropenem sodium, in particular to a method for removing high-content residual palladium in crude faropenem sodium. Background technique [0002] Formula (I) faropenem sodium is a penem antibiotic developed by Japan Suntory Company, which was first listed in Japan in 1997, and its chemical name is: (5R, 6S)-6-[(1R)-1-hydroxyethyl Base]-7-oxo-3-[(2R)-2-tetrahydrofuryl]-4-thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt, Usually with 2.5 water molecules. The drug has the characteristics of broad antibacterial spectrum, strong antibacterial activity, and stability to β-lactammycetes. It is available for oral administration and injection, and is highly effective against Gram-positive, negative and anaerobic bacteria. [0003] European Patent 199446, Chinese Patent 101125857A and Han Hongna et al. (Chinese Journal of Pharm...

Claims

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Application Information

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IPC IPC(8): C07D499/893C07D499/18
Inventor 陈芬儿黄建平赵磊陈旭翔
Owner FUDAN UNIV
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