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Synthesis method of 9-desoxy-9-homoerythromycin A(Z) oxime

A synthesis method and technology of erythromycin, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve problems such as affecting stable existence, inability to obtain products, yellow color, etc., and achieve less impurities and better operation. Simple, color-free effect

Active Publication Date: 2016-04-06
湖北回盛生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Among the two configurations of 9-deoxy-9-homoerythromycin A oxime, the E type is a stable configuration, and the Z type is an unstable configuration, so in the preparation process of the Z type, reaction, distillation, extraction, adjustment Various steps such as pH value, concentration, recrystallization, and small changes in temperature may affect the stable existence of Z-type, resulting in impurity, low yield, and yellow color of the obtained product, which will affect subsequent reactions. Operate according to the literature , can not get good product

Method used

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  • Synthesis method of 9-desoxy-9-homoerythromycin A(Z) oxime
  • Synthesis method of 9-desoxy-9-homoerythromycin A(Z) oxime
  • Synthesis method of 9-desoxy-9-homoerythromycin A(Z) oxime

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Experimental program
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Effect test

Embodiment 1

[0037] A kind of synthetic method of 9-deoxy-9-homoerythromycin A (Z) oxime, its step is:

[0038] Add 100g of 9-deoxy-9-homoerythromycin A (E) oxime into a three-necked flask, then add 500ml of dichloromethane, stir until 9-deoxy-9-homoerythromycin A (E) oxime is completely dissolved, then add 6.8g of triethylamine was stirred at 3°C ​​for 58 hours. After stirring for 54-57 hours, the reaction system changed from a clear transparent liquid to a milky emulsion, and continued to stir for 24 hours. At this time, the reaction was completed, filtered, and the obtained The filter residue was washed with 50ml of dichloromethane at 3°C ​​to obtain a white solid, which was vacuum-dried at 40°C and -0.098Mpa for 5 hours to obtain 88.9g of 9-deoxy-9-homoerythromycin A(Z) oxime . The obtained 9-deoxy-9-homoerythromycin A(Z) oxime is a white solid with a melting point of 158.7°C-162.0°C (157-164°C in EP0503949), a purity of 93.06%, and a yield of 90.43%. The results of the infrared spec...

Embodiment 2

[0044] A kind of synthetic method of 9-deoxy-9-homoerythromycin A (Z) oxime, its step is:

[0045] Add 100g of 9-deoxy-9-homoerythromycin A (E) oxime into a three-necked flask, then add 500ml of ethyl acetate, stir until 9-deoxy-9-homoerythromycin A (E) oxime is completely dissolved, then add 4.92g of diethylamine, stirred at 0°C for 48 hours, after stirring for 46-47 hours, the reaction system changed from a clear liquid to a milky emulsion, and continued to stir for 24 hours. At this time, the reaction was completed, filtered, and the obtained The filter residue was washed with 50ml of ethyl acetate at 0°C to obtain a white solid, which was vacuum-dried at 40°C and -0.098Mpa for 5 hours to obtain 91.1g of 9-deoxy-9-homoerythromycin A(Z) oxime . The resulting 9-deoxy-9-homoerythromycin A(Z) oxime is a white solid with a melting point of 158.8°C to 162.3°C (EP0503949 is 157-164°C), a purity of 93.01%, and a yield of 87.69%. The result is: IR(KBr)σ, cm -1 : 3550 (N-OH), 1725...

Embodiment 3

[0049] A kind of synthetic method of 9-deoxy-9-homoerythromycin A (Z) oxime, its step is:

[0050] Add 100g of 9-deoxy-9-homoerythromycin A (E) oxime into a three-necked flask, then add 500ml of pentanone, stir until 9-deoxy-9-homoerythromycin A (E) oxime is completely dissolved, then add 2.69 g sodium hydroxide, stirred at 5°C for 40 hours, after stirring for 38-39 hours, the reaction system changed from a clear liquid to a milky emulsion, and continued to stir for 24 hours. At this time, the reaction was completed, filtered, and the obtained The filter residue was washed with 50ml of 5°C pentanone to obtain a white solid, which was vacuum-dried at 40°C and -0.098Mpa for 5 hours to obtain 87.1g of 9-deoxy-9-homoerythromycin A(Z) oxime. The obtained 9-deoxy-9-homoerythromycin A(Z) oxime is a white solid with a melting point of 158.5°C-162.2°C (157-164°C in EP0503949), a purity of 93.12%, and a yield of 83.94%. The results of the infrared spectrum are: IR(KBr)σ, cm -1 : 3550 ...

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Abstract

The invention discloses a synthesis method of 9-desoxy-9-homoerythromycin A(Z) oxime, which comprises the following steps: adding 9-desoxy-9-homoerythromycin A(E) oxime into an organic solvent, wherein the mass-volume ratio of the 9-desoxy-9-homoerythromycin A(E) oxime to the organic solvent is 1g:(3-10)ml; stirring until the 9-desoxy-9-homoerythromycin A(E) oxime is completely dissolved, and adding an alkali, wherein the mole ratio of the 9-desoxy-9-homoerythromycin A(E) oxime to the alkali is 1:(0.2-1.0); stirring at 0-5 DEG C for 64-82 hours; and after the reaction finishes, filtering, washing the obtained filter residue with a 0-5-DEG C organic solvent to obtain a white solid, and carrying out vacuum drying on the white solid to obtain the 9-desoxy-9-homoerythromycin A(Z) oxime finished product. The method is very simple in technical process and very convenient to operate. The synthesized 9-desoxy-9-homoerythromycin A(Z) oxime has the advantages of high purity, no color change and high yield.

Description

technical field [0001] The invention relates to the technical field of synthesis methods of macrolide drug raw materials, in particular to a synthesis method of 9-deoxy-9-homoerythromycin A(Z) oxime. Background technique [0002] Gamimycin is a second-generation macrolide aza-7α antibiotic, which is a derivative of erythromycin, and its structural formula is as follows: [0003] [0004] 9-deoxy-9-homoerythromycin A oxime is an intermediate in the synthesis of macrolide antibiotics such as roxithromycin, clarithromycin, and azithromycin. It has two different configurations, E and Z, of which 9-deoxy- 9-homoerythromycin A(E) oxime is the raw material for synthesizing azithromycin, and 9-deoxy-9-homoerythromycin A(Z) oxime is the raw material for synthesizing garamimycin, which is obtained by E-type configuration conversion. [0005] [0006] 9-deoxy-9-homoerythromycin A(E) oxime 9-deoxy-9-homoerythromycin A(Z) oxime [0007] Gamimycin is a veterinary antibiotic produc...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00
CPCC07H1/00C07H17/08
Inventor 张卫元沈华李硕郝康代兵王线郑春红高松左三龄葛健
Owner 湖北回盛生物科技有限公司
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