Supercharge Your Innovation With Domain-Expert AI Agents!

Preparation method of erythromycin 6,9-imino ether compound

A technology of imino ether and erythromycin, which is applied to the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., to achieve the effects of industrial production, high yield, and simple operation

Active Publication Date: 2016-11-09
LIANYUNGANG DUXIANG CHEM
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no literature report on a new method of one-step synthesis of erythromycin 6, 9 imine ether from erythromycin thiocyanate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of erythromycin 6,9-imino ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Preparation of erythromycin 6, 9 imine ether compound: In an air atmosphere, add 10 mmol erythromycin thiocyanate, 10 mmol N-glycolamide and 50 ml acetonitrile to a 100 ml two-necked flask, and stir at room temperature for 10 minutes Finally, 3 mmol of concentrated sulfuric acid was added dropwise, and then a cooling tube was placed on the shelf and heated to 80°C with an oil bath under magnetic stirring, and reacted for 8 hours. Remove the oil bath, add 20 ml of water to the reaction solution, extract three times with 60 ml of ethyl acetate, combine the organic phases and wash with anhydrous MgSO 4 Dry for 30 minutes, filter; the filtrate is evaporated to dryness with a rotary evaporator, add water, adjust the pH value of the solution to 10-12 with NaOH solution, precipitate out, filter, and dry to obtain the erythromycin 6, 9 imino ether product with a yield of 86 %. The product has a melting point of 129-130°C. The nuclear magnetic analysis data are as follows: 1 ...

Embodiment 2

[0017] Preparation of erythromycin 6, 9 imine ether compound: Add 10 mmol erythromycin thiocyanate, 15 mmol N-hydroxypropionamide and 50 ml propionitrile to a 100 ml two-necked flask in an air atmosphere, and stir at room temperature After 10 minutes, 5 mmol of methanesulfonic acid was added dropwise, and then a cooling tube was placed on the shelf and heated to 100° C. with an oil bath under magnetic stirring, and reacted for 12 hours. Remove the oil bath, add 20 ml of water to the reaction solution, extract three times with 60 ml of ethyl acetate, combine the organic phases and wash with anhydrous MgSO 4 Dry for 30 minutes, filter; the filtrate is evaporated to dryness with a rotary evaporator, add water, adjust the pH value of the solution to 10-12 with NaOH solution, precipitate out, filter, and dry to obtain the erythromycin 6, 9 imino ether product with a yield of 83 %.

Embodiment 3

[0019] Preparation of erythromycin 6, 9 imine ether compound: in air atmosphere, add 10mmol erythromycin thiocyanate, 16 mmol N-hydroxybenzamide and 50 ml dioxane to a 100 ml two-necked flask, After stirring at room temperature for 10 minutes, 4 mmol of benzenesulfonic acid was added dropwise, and then a cooling tube was placed on the rack and heated to 110° C. with an oil bath under magnetic stirring, and reacted for 24 hours. Remove the oil bath, add 20 ml of water to the reaction solution, extract three times with 60 ml of ethyl acetate, combine the organic phases and wash with anhydrous MgSO 4 Dry for 30 minutes, filter; the filtrate is evaporated to dryness with a rotary evaporator, add water, adjust the pH value of the solution to 10-12 with NaOH solution, precipitate out, filter, and dry to obtain the erythromycin 6, 9 imino ether product with a yield of 80 %.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a preparation method of an erythromycin 6,9-imino ether compound. According to the method, a reaction of acid-catalyzed erythromycin thiocyanate and N-hydroxyamide is adopted, an oximation reaction of erythromycin and a rearrangement reaction of erythromycin oxime are conducted in a one-step mode, and erythromycin 6,9-imino ether is generated. The preparation method of the compound comprises the preparation steps that erythromycin thiocyanate, N-hydroxyamide and acid are taken and added into an organic solvent, heating is conducted, extracting, drying by distillation and water adding are conducted after the reaction is completed, the pH value of the solution is adjusted to range from 10 to 12, precipitating, filtering and drying are conducted, and the erythromycin 6,9-imino ether product is obtained. According to the preparation method, the erythromycin 6,9-imino ether compound is synthesized in a one-step mode, operation is easy, the method is economical and efficient, a venomous sulfonyl chloride reagent is not used, environmental pollution is less, the yield is high, and the application prospect is wide.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of erythromycin 6,9 imine ether compound. Background technique [0002] Azithromycin is the representative variety of the second-generation erythromycin. Compared with erythromycin, it increases the blood concentration, enhances the curative effect, prolongs the half-life, reduces the dosage and side effects, and its excellent cost performance makes it the most widely used drug at present. One of the antibiotics. The current production process of azithromycin is as follows: 1. Erythromycin oxime is obtained by oximation reaction of erythromycin thiocyanate or erythromycin; 2. Erythromycin oxime is obtained by Beckmann rearrangement reaction to obtain erythromycin 6, 9 imino ether ; 3. Erythromycin 6, 9 imine ether reduction reaction to obtain dihydrohomoerythromycin; 4. Dihydrohomoerythromycin methylation reaction to obtain azithromycin. Among t...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07H17/00C07H1/00
CPCC07H1/00C07H17/00
Inventor 徐晨王笃政谢建新王川民郑晓斌
Owner LIANYUNGANG DUXIANG CHEM
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com