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Preparation method of ceftibuten

A technology of cefbutene and cefaclor mother nucleus, which is applied in the field of medicine and chemical industry and achieves the effects of high yield, simple operation and high purity

Active Publication Date: 2015-12-16
山东昌邑四方医药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Utilize D301 type ion-exchange resin as catalyzer, be that the method for raw material preparation ceftibuten by cefaclor nucleus 7-amino-3-chloro-3-cephem-4-carboxylic acid has not been reported yet, and cefaclor nucleus 7-ANCA The synthesis of mainly utilizes penicillins and cephalosporins as raw materials for preparation

Method used

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  • Preparation method of ceftibuten
  • Preparation method of ceftibuten
  • Preparation method of ceftibuten

Examples

Experimental program
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Effect test

Embodiment 1

[0025] In a 100 ml three-necked flask, add 2.4 grams (0.01 moles) of cefaclor core, 15 milliliters of methyl tetrahydrofuran, and 0.4 grams (0.017 moles) of magnesium powder. After reacting at 30°C until the magnesium powder disappears, add 10 milliliters of distilled water, Stir for 10 minutes, stand to separate the layers, separate the methyl tetrahydrofuran organic layer and dry it with anhydrous magnesium sulfate. After filtering, add 0.7 g of Styrene-DVB (D301R) resin, 2-(2-benzyloxycarbonylaminothiazole-4- base)-5-benzyloxycarbonyl-2-pentenoic acid 5 g (0.011 moles), reacted at 30°C for 3 hours, filtered off the Styrene-DVB (D301R) resin after the reaction, distilled off methyl tetrahydrofuran, and added iso 10 ml of isopropanol and 20 ml of NaOH (30%) aqueous solution were reacted at 30°C for 1 hour, then cooled to 20°C. Extracted three times with 10×3 ml of dichloromethane, added concentrated HCl dropwise to the aqueous solution layer at 0°C to adjust the pH=5-6, left ...

Embodiment 2

[0027] In a 100 ml three-necked flask, add 2.4 grams (0.01 moles) of cefaclor core, 15 milliliters of methyl tetrahydrofuran, and 0.4 grams (0.017 moles) of magnesium powder. After reacting at 50 ° C until the magnesium powder disappears, add 10 milliliters of distilled water, Stir for 10 minutes, stand to separate the layers, separate the methyl tetrahydrofuran organic layer and dry it with anhydrous magnesium sulfate. After filtering, add 1.2 grams of Styrene-DVB (D301R) resin, 2-(2-benzyloxycarbonylaminothiazole-4- base)-5-benzyloxycarbonyl-2-pentenoic acid 5 g (0.011 moles), reacted at 30°C for 1 hour, filtered off the Styrene-DVB (D301R) resin after the reaction, distilled off methyl tetrahydrofuran, and added iso 10 ml of isopropanol and 20 ml of NaOH (30%) aqueous solution were reacted at 30°C for 1 hour, then cooled to 20°C. Extracted three times with 10×3 ml of dichloromethane, added concentrated HCl dropwise to the aqueous solution layer at 0°C to adjust the pH=5-6, ...

Embodiment 3

[0029] In a 100 ml three-necked flask, add 2.4 grams (0.01 moles) of cefaclor core, 15 milliliters of methyl tetrahydrofuran, and 0.4 grams (0.017 moles) of magnesium powder. After reacting at 30°C until the magnesium powder disappears, add 10 milliliters of distilled water, Stir for 10 minutes, stand to separate the layers, separate the methyl tetrahydrofuran organic layer and dry it with anhydrous magnesium sulfate. After filtering, add 0.7 g of Styrene-DVB (D301T) resin, 2-(2-benzyloxycarbonylaminothiazole-4- base)-5-benzyloxycarbonyl-2-pentenoic acid 5 g (0.011 moles), reacted at 10°C for 3 hours, filtered off Styrene-DVB (D301T) resin at the end of the reaction, distilled off methyl tetrahydrofuran, and added iso 10 ml of isopropanol, 20 ml of NaOH (30%) aqueous solution, reacted at 20°C for 1 hour, extracted three times with 10×3 ml of dichloromethane, added concentrated HCl dropwise at 0°C to the aqueous solution to adjust the pH to 5-6, and statically Crystals were pre...

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Abstract

The invention provides a preparation method of ceftibuten. The preparation method comprises the steps of adding cefaclor nucleus, methyltetrahydrofuran and magnesium powder into a reactor, and reacting until the magnesium powder disappears; then, adding a proper quantity of distilled water, stirring, standing for layering, separating out an organic layer, and drying by using anhydrous magnesium sulfate; after filtering, adding D301 week basic ion exchange resin and 2-(2-carbobenzoxy-aminothiazole-4-yl)-5-carbobenzoxy-2-pentenoic acid, and reacting at a certain temperature for a certain time; after ending the reaction, filtering to remove the week basic ion exchange resin; and then, hydrolyzing to obtain a target product, namely ceftibuten. The method is a novel preparation method of ceftibuten, is high in product yield and purity as well as simple and convenient in operation, is a green and clean production process and is suitable for industrial production on a certain scale; and the cefaclor nucleus is a main product in the company, and a sustainable development technology of the company is to prepare ceftibuten serving as a mainly developed variety in the Tenth Five-year Plan period from the product of the company.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a method for preparing ceftibuten starting from a cefaclor mother nucleus under the action of a D301 type weakly basic anion exchange resin catalyst. Background technique [0002] Ceftibuten is a third-generation oral broad-spectrum cephalosporin developed by Shionogi Company in Japan, which has strong antibacterial effect on most Gram-negative bacilli and some positive cocci - Lactamase is highly stable and has post-antibiotic effects; it has the characteristics of broad antibacterial spectrum, strong antibacterial activity, and high bioavailability. It is used to treat various infections caused by sensitive strains, including upper respiratory tract infections, lower respiratory tract infections, and Urinary system infection, enteritis and gastroenteritis, etc. [0003] The chemical name of ceftibuten is (+)-(6R,7R)-7β-[(Z)-2-(2-amino-4-thiazole)-4-car...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/04
CPCC07D501/04C07D501/22
Inventor 孙会顾士崇裴文
Owner 山东昌邑四方医药化工有限公司
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