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Method for preparing sulbenicillin disodium

A technology of sulfobenicillin sodium and sulfophenylacetic acid, applied in directions such as organic chemistry, can solve the problems of harsh operating conditions, unsatisfactory yield, long reaction time, etc., and achieves improved reaction temperature, reduced energy consumption, and high reaction yield Effect

Inactive Publication Date: 2010-12-15
HUNAN SANQING PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Adopt this method to prepare sulbenicillin sodium in the prior art, its reaction time is long, and productive rate is also undesirable, especially purity is not high, and operating condition is harsher, brings inconvenience to suitability for industrialized production

Method used

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  • Method for preparing sulbenicillin disodium
  • Method for preparing sulbenicillin disodium

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Stir and dissolve 52.4g of α-sulfophenylacetic acid in 100mL of ether, add 115mL of thionyl chloride dropwise at -2°C, add dropwise 2.0ml of N,N-diisopropylethylamine, and then The reaction was stirred under low pressure for 1.5 hours. After the reaction was completed, distilled to dryness under reduced pressure, and repeated 2 times to wash the residue after distillation with ether, and then distilled to dryness under reduced pressure to obtain 58.1 g of α-sulfophenylacetyl chloride with a yield of 81.0%. ;

[0038] Add 20.5g of 6-APA into a mixed solvent of 50mL of water, 29mL of ethanol and 10mL of 2-methyltetrahydrofuran, keep the temperature at 15°C, then add dropwise 10% sodium hydroxide solution to adjust the pH to 7.0, and stir at 15°C To the complete dissolution of the solid, keep the temperature and add dropwise the butyl acetate solution containing 31.2g α-sulfophenylacetyl chloride, wherein the butyl acetate solution of α-sulfophenylacetyl chloride is evenly...

Embodiment 2

[0041] Stir and dissolve 52.4g of α-sulfophenylacetic acid in 100mL of ether, add 89mL of thionyl chloride dropwise at -3°C, add dropwise 1.2ml of N,N-diisopropylethylamine, and then Stirring and reacting for 2.5 hours, after the reaction was completed, distilled to dryness under reduced pressure, repeated 2 times to wash the residue after distillation with ether, and then distilled to dryness under reduced pressure to obtain 61.2g α-sulfophenylacetyl chloride, yield 85.4 %;

[0042] Add 20.5g of 6-APA into a mixed solvent of 50mL of water, 25mL of ethanol and 12.5mL of 2-methyltetrahydrofuran, keep the temperature at 25°C, and then add dropwise a 15% sodium hydroxide solution to adjust the pH to 6.0, at 25°C Stir until the solid is completely dissolved, and then add dropwise a butyl acetate solution containing 34.0 g of α-sulfophenylacetyl chloride at the temperature. After the dropwise addition, maintain the pH of the reaction solution at 6.0, and react at room temperature f...

Embodiment 3

[0045] Stir and dissolve 52.4g of α-sulfophenylacetic acid in 100mL of ether, add 160mL of thionyl chloride dropwise at -5°C, add dropwise 1.6ml of N,N-diisopropylethylamine, and then Stirring and reacting for 2.0 hours, after the reaction was completed, distilled under reduced pressure to dryness, repeated 2 times to wash the residue after distillation with ether, and then distilled under reduced pressure to dryness to obtain 59.2g α-sulfophenylacetyl chloride, yield 82.6 %;

[0046] Add 20.5g of 6-APA into a mixed solvent of 50mL of water, 34mL of ethanol and 8.5mL of 2-methyltetrahydrofuran, keep the temperature at 20°C, and then add dropwise a 10% sodium hydroxide solution to adjust the pH to 5.6, at 20°C Stir until the solid is completely dissolved, then add dropwise a butyl acetate solution containing 30.0 g of α-sulfophenylacetyl chloride at this temperature, after the dropwise addition, maintain the pH of the reaction solution at 5.6, and react at room temperature for ...

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Abstract

The invention provides a method for preparing sulbenicillin disodium. The method comprises the following steps of: preparing alpha-sulfophenylacetyl chloride from alpha-sulfophenylacetic acid; reacting the alpha-sulfophenylacetyl chloride with 6-aminopenicillanic acid (APA) in the mixed solvents of water, ethanol and tetrahydro-2-methylfuran under the condition of the pH value of 5.6 to 7.0 and the temperature of 15 to 25 DEG C for 20 to 40 minutes to obtain crude sulbenicillin disodium; and obtaining the aqueous solution of the sulbenicillin disodium by post treatment and then cooling and drying the aqueous solution of the sulbenicillin disodium to obtain the final product, namely the sulbenicillin disodium. The method has the advantages of reducing energy consumption and saving production cost along with simple process, mild reaction condition and high yield.

Description

technical field [0001] The present invention relates to a kind of preparation method of sulbenicillin sodium, specifically, relate to the preparation method of sulbenicillin sodium. Background technique [0002] Sulbenicillin sodium, the English name is sulbenicillin disodium, the Chinese chemical name is: (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetamido)-7- Oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt. [0003] Its structural formula is: [0004] [0005] Molecular formula is C 16 h 16 N 2 Na 2 o 7 S 2 , the molecular weight is 458.42. [0006] Sulbenicillin sodium is an optically active broad-spectrum semi-synthetic penicillin developed by Takeda Pharmaceutical Company in Japan. It was launched in the market in 1973 and included in the Chinese Pharmacopoeia in 1990. Sulbenicillin sodium combines with the penicillin-binding protein on the cell membrane to hinder the synthesis of bacterial cell wall mucopeptides, making it unable to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/62C07D499/16
Inventor 张舰
Owner HUNAN SANQING PHARMA
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