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Synthesizing method of 3-N-ethyl gentamicin C1a

A technology of ethyl gentamicin and diacetyl gentamicin, applied in the field of organic chemical synthesis, can solve problems such as difficulty in obtaining impurities, no standard product sales of 3-N-ethyl gentamicin C1a, etc. , to achieve the effect of low cost, short time and less environmental pollution

Inactive Publication Date: 2018-02-02
WUXI JIMIN KEXIN SHANHE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] 3-N-ethyl gentamicin C1a of the present invention is one of the main impurities remaining in the etimicin sulfate raw material and preparation, and is also the most difficult to obtain impurity. There is no 3-N-ethyl gentamicin at home and abroad. There is no relevant literature report on the sale of the standard product of gentamicin C1a

Method used

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  • Synthesizing method of 3-N-ethyl gentamicin C1a
  • Synthesizing method of 3-N-ethyl gentamicin C1a
  • Synthesizing method of 3-N-ethyl gentamicin C1a

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1, 3-N-ethyl gentamicin C 1a

[0036] a. Put 8 mL of ethylene glycol dimethyl ether, 5 mL of hexamethyldisilazane, and 0.02 mL of concentrated sulfuric acid into a 100 mL dry round-bottomed flask equipped with a reflux condenser with a drying tube. After stirring evenly, add 2" ,6″-N,N-Diacetylgentamycin C 1a 1.0g, heated to reflux, reacted for 2h. Change the distillation device to heat at normal pressure to steam out the solvent ethylene glycol dimethyl ether.

[0037] b. Cool down to 0-10°C, add 9mL of dichloromethane, then add dropwise 0.2mL of acetaldehyde at 0-10°C, and stir for 1h. Add 0.5 g of potassium borohydride, react for 0.5 h, add 3 mL of boric acid buffer solution (1.0 g of boric acid and 3.0 mL of deionized water are stirred to dissolve, adjust pH=10 with sodium hydroxide), and stir for 1.5 h.

[0038] c. Add 10% sodium hydroxide and stir for 0.5h, heat and distill under normal pressure until the liquid temperature is 100°C, and distill of...

Embodiment 2

[0040] Embodiment 2, 3-N-ethyl gentamicin C 1a

[0041] a. Put 8 mL of ethylene glycol dimethyl ether, 5 mL of hexamethyldisilazane, and 0.02 mL of concentrated sulfuric acid into a 100 mL dry round-bottomed flask equipped with a reflux condenser with a drying tube. After stirring evenly, add 2" ,6″-N,N-Diacetylgentamycin C 1a 1.0g, heated to reflux, reacted for 2h. Change the distillation device to heat at normal pressure to steam out the solvent ethylene glycol dimethyl ether.

[0042] b. Cool down to 0-10°C, add 9mL of dichloromethane, then add dropwise 0.2mL of acetaldehyde at 0-10°C, and stir for 1h. Add 0.5 g of potassium borohydride, react for 0.5 h, add 3 mL of boric acid buffer solution (1.0 g of boric acid and 3 mL of deionized water are stirred to dissolve, adjust pH=10 with sodium hydroxide), and stir for 1.5 h.

[0043]c. Add 10% sodium hydroxide and stir for 0.5h, heat and distill under normal pressure until the liquid temperature is 100°C, and distill off p...

Embodiment 3

[0045] Embodiment 3, 3-N-ethyl gentamicin C 1a

[0046] a. Put 8 mL of ethylene glycol dimethyl ether, 5 mL of hexamethyldisilazane, and 0.02 mL of concentrated sulfuric acid into a 100 mL dry round-bottomed flask equipped with a reflux condenser with a drying tube. After stirring evenly, add 2" ,6″-N,N-Diacetylgentamycin C 1a 1.0g, heated to reflux, reacted for 2h. Change the distillation device to heat at normal pressure to steam out the solvent ethylene glycol dimethyl ether.

[0047] b. Cool down to 0-10°C, add 9mL of dichloromethane, then add dropwise 0.2mL of acetaldehyde at 0-10°C, and stir for 1h. Add 0.5 g of potassium borohydride, react for 0.5 h, add 3 mL of boric acid buffer solution (1.0 g of boric acid and 3 mL of deionized water are stirred to dissolve, adjust pH=10 with sodium hydroxide), and stir for 1.5 h.

[0048] c. Add 10% sodium hydroxide and stir for 0.5h, heat and distill under normal pressure until the liquid temperature is 100°C, and distill off ...

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Abstract

The present invention relates to a kind of synthetic method of 3-N-ethyl gentamicin C1a, the method comprises the following steps: ethylene glycol dimethyl ether, hexamethyldisilazane, concentrated sulfuric acid, 2 ", 6" ‑N,N‑Diacetylgentamycin C1a was put into a round-bottomed flask and refluxed. After the reactants were dissolved, part of the solvent was distilled off. Dichloromethane was added and stirred at 10°C, and acetaldehyde was added dropwise. After the reaction was completed, potassium borohydride and boric acid buffer were added to stir the reaction, and part of the solvent was distilled off under normal pressure. Add 10%-20% sodium hydroxide solution, heat to reflux, cool down to room temperature, and concentrate the reaction system. Desalting, the target compound 3-N-ethyl gentamycin C1a was obtained by separation.

Description

technical field [0001] The present invention relates to an organic chemical synthesis method, specifically a 2", 6"-N, N-diacetyl gentamycin C 1a Synthesis of 3-N-ethylgentamycin C 1a Methods. Background technique [0002] Etimicin sulfate is a new generation of semi-synthetic aminoglycoside antibiotics with independent intellectual property rights, high efficiency, low toxicity, and resistance to drug-resistant bacteria. It is the only anti-infective drug that has obtained the national first-class new drug certificate. Its preparation etimicin sulfate injection is suitable for Escherichia coli, Klebsiella pneumoniae, Serratia spp., Citrobacter spp., Enterobacter spp., Acinetobacter spp., Proteus spp. Various infections caused by blood bacillus, Pseudomonas aeruginosa and staphylococcus. Clinical studies have shown that this product has a good curative effect on the following infections: [0003] Respiratory tract infection: such as acute bronchitis, acute exacerbation o...

Claims

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Application Information

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IPC IPC(8): C07H15/236C07H1/00
CPCC07H15/236C07H1/00
Inventor 王晓霞吴凌云闵江
Owner WUXI JIMIN KEXIN SHANHE PHARMA
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