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A kind of refining method of cefprozil

A technology of cefprozil and refining method, which is applied in the direction of organic chemistry, can solve the problems of cumbersome steps, low yield, waste of raw materials, etc., and achieve the effect of simple synthesis route, high total product yield and easy operation

Active Publication Date: 2020-06-16
SHANDONG YUXIN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The preparation method of the prior art has cumbersome steps and many side reactions, and is not suitable for industrial production; or the yield is low, raw materials are wasted, and production costs are increased
In addition, in some cases, due to improper control of the production process, the purity of the drug did not meet the requirements

Method used

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  • A kind of refining method of cefprozil
  • A kind of refining method of cefprozil
  • A kind of refining method of cefprozil

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Cefprozil crude synthesis

[0029] a. Add 16.72g of compound II, 26.63g of di-tert-butyl dicarbonate, 0.61g of 4-dimethylaminopyridine, and 600ml of N,N-dimethylformamide into the reaction flask in sequence, and control the temperature at 30-40°C Under nitrogen, the reaction was stirred for 6 h under nitrogen. After the reaction, it was washed with deionized water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 23.97 g of compound III with a yield of 89.8% and a purity of 99.75%.

[0030] b. Under the protection of nitrogen, dissolve 23.97g of compound III in 320ml of anhydrous dichloromethane, add 12.41g of potassium carbonate, then dropwise add 0.0898mol oxalyl chloride, stir at room temperature for 3h, then add 32.82g of compound IV, Stir at room temperature for 4 h. After the reaction, wash with deionized water and dry over anhydrous sodium sulfate. Evaporate and remove the solvent to obtain 50.96 g of ...

Embodiment 2

[0035] (1) Synthesis of Cefprozil Crude Product

[0036] a. Add 16.72g of compound II, 26.63g of di-tert-butyl dicarbonate, 0.61g of 4-dimethylaminopyridine, and 600ml of N,N-dimethylformamide into the reaction flask in sequence, and control the temperature at 30-40°C Under nitrogen, the reaction was stirred under nitrogen for 6 h. After the reaction, it was washed with deionized water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 24.31 g of compound III with a yield of 91.1% and a purity of 99.79%.

[0037] b. Under the protection of nitrogen, dissolve 24.31g of compound III in 320ml of anhydrous dichloromethane, add 37.77g of potassium carbonate, then dropwise add (0.0911mol) oxalyl chloride, stir at room temperature for 3h, then add compound IV33. 29 g, stirred at room temperature for 4 h, after the reaction, washed with deionized water and dried over anhydrous sodium sulfate, and evaporated to remove the solvent...

Embodiment 3

[0042] (1) Synthesis of Cefprozil Crude Product

[0043] a. Add compound II 16.72, 29.29 g of di-tert-butyl dicarbonate, 1.22 g of 4-dimethylaminopyridine, and 600 ml of tetrahydrofuran in sequence in the reaction flask, and control the temperature at 30-40 ° C, and stir the reaction in nitrogen for 6 h , after the reaction was completed, it was washed with deionized water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 24.37 g of compound III with a yield of 91.3% and a purity of 99.78%.

[0044] b. Under nitrogen protection, dissolve 24.31g of compound III in 320ml of anhydrous dichloromethane, add 25.24g of potassium carbonate, then dropwise add (0.0913mol) oxalyl chloride, stir at room temperature for 3h, then add compound IV33. 37g, stirred at room temperature for 4h, after the reaction, washed with deionized water and dried over anhydrous sodium sulfate, and evaporated to remove the solvent to obtain 51.98g of s...

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Abstract

The invention discloses a cefprozil refining method. The method includes: (1) dissolving a crude cefprozil product in a mixed solvent of deionized water, ethanol and dichloromethane, conducting heating reflux dissolution to prepare a saturated or supersaturated solution; (2) performing cooling to 20-30DEG C, adding activated carbon for decolorization, conducting filtration, cooling the filtrate to5DEG C-10DEG C, performing crystallization for 1h, conducting cooling to 0DEG C-5DEG C, and performing crystal growing; (3) conducting filtering, and performing leaching with ethanol to obtain a white solid; and (4) placing the white solid obtained by step (3) in a vacuum drying box, conducting vacuum pumping, and performing drying for 3h or more, thus obtaining cefprozil crystals. The refining method provided by the invention remarkably improves the product quality, and is simple in operation, thus being suitable for industrial production.

Description

technical field [0001] The invention relates to the field of synthesis of medicines, in particular to a synthesis method of the anti-infection drug cefprozil. Background technique [0002] Cefprozil is a second-generation cephalosporin antibiotic with a broad-spectrum antibacterial effect. Blood bacteria etc. also have inhibitory effect. The bactericidal mechanism is to hinder the synthesis of bacterial cell walls, which is safe and has extremely low adverse reactions. Cefprozil has been recorded in the United States Pharmacopoeia and is one of the varieties recommended by American clinicians. It is clinically used for mild to moderate skin infections and respiratory tract infections caused by sensitive bacteria. [0003] Cefprozil (Cefprozil), the chemical name is (6R,7R)-7-[(2R)-amino(4-hydroxyphenyl)acetamido]-8-oxo-3-(1-propenyl)-5 - Thio-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. Its structural formula is shown in formula I: [0004] [0005] The preparatio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/22C07D501/12
CPCC07D501/12C07D501/22
Inventor 刘振腾李震王加成张金宝
Owner SHANDONG YUXIN PHARMA CO LTD
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