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Method for preparing 3,2',6'-tri-N-acetyl gentamicin C1a

A technology based on gentamicin and gentamicin, which is applied in the field of preparation of medical raw material intermediates, can solve problems such as yield less than 75%, and achieve the effects of improving yield and small repulsive force

Active Publication Date: 2012-09-05
CHANGZHOU FANGYUAN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the yield is less than 75%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0015] The preparation method of the present embodiment has the following steps:

[0016] ①Add 1000mL of methanol solvent and 90g of gentamicin C 1a (0.2mol) and 110g of zinc acetate, stirred to fully dissolve, gentamicin C 1a Coordination reaction with zinc acetate to obtain gentamicin C 1a -Zn complexes.

[0017] ②Reduce the temperature of the system in step ① to 0°C to 10°C, add dropwise a mixture of 85mL acetic anhydride (0.9mol), 350mL triethylamine and 150mL tetrahydrofuran to the system in step ① under stirring, and generate 3,2',6'-tri-N-acetylgentamycin C 1a For the acylation reaction of the Zn complex, continue stirring and insulated reaction for 1 h after the dropwise completion. Then add 300mL of purified water to the reacted material, then place it in a rotary evaporator and distill it under vacuum and reduced pressure at a temperature of 60°C until the remaining 300mL of 3,2',6'-tri-N-acetyl Gentamicin C 1a -Concentrated solution of Zn complex, then cooled ...

Embodiment 2～ Embodiment 5）

[0020] The preparation method of each embodiment is basically the same as that of Example 1, and the difference is that the acetic anhydride used in step 2. and gentamicin C 1a The molar ratio of different, the impact of the amount of acetic anhydride on the reaction yield is shown in Table 1.

[0021] Table 1

[0022] Acetic anhydride and gentamicin C 1a molar ratio yield Example 1 4.5∶1 94.9% Example 2 5∶1 93.6% Example 3 4∶1 90.2% Example 4 3.5∶1 87.9% Example 5 3∶1 85.4%

[0023] As can be seen from Table 1, increasing the amount of acetic anhydride increases the reaction yield, and when the molar ratio reaches 4.5:1, increasing the amount of acetic anhydride decreases the yield instead. Therefore, acetic anhydride and Qingda Mycin C 1a The optimum molar ratio is 4.5:1.

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Abstract

The invention discloses a method for preparing 3,2',6'-tri-N-acetyl gentamicin C1a, which comprises the following steps of: (1) performing coordination reaction on gentamicin C1a and zinc acetate in a methanol solvent at the temperature of between 15 and 25 DEG C to prepare a gentamicin C1a-Zn complex; (2) reducing the temperature of the system of the step (1) to between 0 and 10 DEG C, dropwise adding mixed liquid consisting of acetic anhydride, triethylamine and tetrahydrofuran with stirring for acylation reaction to prepare 3,2',6'-tri-N-acetyl gentamicin C1a-Zn complex, after dropwise adding, continuously stirring and reacting for 1 to 2 hours, and adding water and distilling under reduce pressure to prepare concentrated solution containing the 3,2',6'-tri-N-acetyl gentamicin C1a-Zn complex; and (3) performing after treatment on the concentrated solution prepared by the step (2) to prepare a 3,2',6'-tri-N-acetyl gentamicin C1a finished product. The method has the advantage of higher yield.

Description

technical field [0001] The invention relates to a preparation method of a medical raw material intermediate, in particular to a 3,2',6'-tri-N-acetyl gentamicin C 1a method of preparation. Background technique [0002] Chinese patent document CN1040177C (application number 93112412.3) discloses a 1-N-ethyl gentamicin C 1a Pharmaceutical formulations and preparation methods of salts thereof. [0003] of which gentamicin C 1a Preparation of 3,2',6'-tris-N-acetylgentamycin C 1a The method is: at room temperature, the gentamicin C 1a Dissolve in water and non-protic polar organic solvents (such as dimethylformamide, dimethyl sulfoxide, etc.), then add cobalt acetate, and then add dropwise the THF solution of acetic anhydride until the reaction is completed. The post-treatment is: dilute the reaction solution with water, and then pass through the strongly acidic 732 (H + ) resin column adsorption, followed by water washing, ammonia water analysis, and concentration under red...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/236C07H1/00
Inventor 封成军李兴刚胡东辉毕晓明苏晓春狄绍炎
Owner CHANGZHOU FANGYUAN PHARMA
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