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Preparing method of cefuroxime acid and method of removing DCC lactone in preparation process of the cefuroxime acid

A cefuroxime acid, preparation process technology, applied in the field of chemical drug synthesis, to achieve high purity and considerable economic benefits

Active Publication Date: 2014-12-24
GUANGDONG LIGUO PHARMACY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved in the present invention is, aiming at the defects in the prior art that DCC is prone to undergo lactonization reaction under acidic conditions or in the drying process to generate DCC lactone and affect the yield and purity of cefuroxime acid, provide a A method for removing cefuroxime by-products during the preparation of cefuroxime acid, the method can not only remove the produced DCC lactone but also convert DCC lactone into DCC, thereby improving the product yield and quality of cefuroxime acid

Method used

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  • Preparing method of cefuroxime acid and method of removing DCC lactone in preparation process of the cefuroxime acid
  • Preparing method of cefuroxime acid and method of removing DCC lactone in preparation process of the cefuroxime acid
  • Preparing method of cefuroxime acid and method of removing DCC lactone in preparation process of the cefuroxime acid

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Separation of DCC lactone: Take 100g of DCC wet product (moisture content about 30%) produced during the preparation of cefuroxime acid, add 400ml of acetone, stir and dissolve at room temperature, and collect the filtrates (that is, the by-products removed) after filtration DCC in acetone) and undissolved DCC lactone. At this time, about 3 g of DCC lactone was obtained.

[0028] Recovery of DCC lactone: Add 3g of DCC lactone into a mixed solvent of 7.5ml of acetone and 22.5ml of water, cool down to -20~-15°C, add about 15% sodium hydroxide solution 3ml for hydrolysis reaction, HPLC detection The extent of the hydrolysis reaction. After the hydrolysis is complete, adjust the pH value to 6.0-7.0 with 6mol / L hydrochloric acid, add 1.0g of activated carbon and stir for 30 minutes to decolorize, then filter, wash with 15ml of water, collect the filtrate and lotion, and dissolve it with 6mol / L hydrochloric acid. The pH value of the mixture of the filtrate and washing liqui...

Embodiment 2

[0031] Separation of DCC lactone: Take 100g of DCC wet product (moisture content is about 30%) produced during the preparation of cefuroxime acid, add 200ml of acetone, stir and dissolve at room temperature, and collect the filtrates (that is, the by-products removed) after filtration DCC in acetone) and undissolved DCC lactone. At this time, about 3 g of DCC lactone was obtained.

[0032] Recovery of DCC lactone: Add 3g of DCC lactone to a mixed solvent of 1.8ml of acetone and 18.2ml of water, adjust the temperature to -5~0°C, add about 15% sodium hydroxide solution 2.4ml for hydrolysis reaction, HPLC Check the progress of the hydrolysis reaction. After the hydrolysis is complete, adjust the pH value to 5.0-5.5 with 6mol / L hydrochloric acid, add 1.0g of activated carbon and stir for 15 minutes to decolorize, then filter, wash with 15ml of water, collect the filtrate and lotion, and dissolve it with 6mol / L hydrochloric acid. The pH value of the mixture of the filtrate and th...

Embodiment 3

[0035] Separation of DCC lactone: Take 100g of DCC wet product (moisture content: 30%) produced during the preparation of cefuroxime acid, add 2000ml of acetone, stir and dissolve at room temperature, and collect the filtrate after filtration (i.e. DCC from by-product removal) acetone solution) and insoluble DCC lactone. At this time, about 3 g of DCC lactone was obtained.

[0036] Recovery of DCC lactone: Add 3g of DCC lactone into a mixed solvent of 4ml of acetone and 2ml of water, cool down to 15-20°C, add about 2.8ml of 15% sodium hydroxide solution to carry out hydrolysis reaction, HPLC detects the progress of the hydrolysis reaction degree. After the hydrolysis is complete, first adjust the pH value to 7.5-8.0 with 6mol / L hydrochloric acid, add activated carbon and stir for 20 minutes to decolorize, then filter, wash with 15ml of water, collect the filtrate and lotion, and use 6mol / L hydrochloric acid to dilute the filtrate and The pH value of the mixed solution of the l...

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Abstract

The invention discloses a preparing method of cefuroxime acid and a method of removing a DCC lactone in a preparation process of the cefuroxime acid. The method of removing the DCC lactone includes a separation step, wherein a wet descarbamoyl cefuroxime acid (DCC) product that is generated in the preparation process and contains a cefuroxime side product (the DCC lactone for short) is dissolved into acetone, and the mixture is stirred at room temperature for dissolution, and filtered to remove the DCC lactone insoluble in the acetone to obtain a DCC acetone solution from which the side product is removed. The method of removing the DCC lactone can effectively remove the DCC lactone from the DCC by utilization the property that the DCC lactone is insoluble in the acetone, thus avoiding introduction of side products in a subsequent cefuroxime acid synthesis process and ensuring preparation of the cefuroxime acid with a high purity. The preparing method of the cefuroxime acid, which includes the method of removing the side product, is also disclosed. The yield and the purity of the cefuroxime acid can be increased by the operation of removing the side product.

Description

technical field [0001] The invention belongs to the field of chemical drug synthesis, and relates to a method for removing cefuroxime by-products during the preparation of cefuroxime acid. The present invention also relates to a method for preparing cefuroxime acid comprising the above method for removing by-products. Background technique [0002] Cefuroxime sodium (ester) is the most representative product among the second-generation cephalosporin products. In the prior art, the synthesis of cefuroxime sodium (ester) usually involves the preparation of intermediate cefuroxime acid through hydrolysis, urethane acylation reaction, condensation reaction, etc., and decarbamyl cefuroxime (DCC) is further Intermediates in the synthesis of furoctanoic acid. [0003] During the synthesis of cefuroxime acid, since DCC needs to be crystallized with acid, a small amount of DCC undergoes lactonization reaction under acidic conditions to produce cefuroxime lactone (DCC lactone), which...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/34C07D501/12
CPCC07D501/12C07D501/34
Inventor 曾良兵
Owner GUANGDONG LIGUO PHARMACY