Preparation method of 2-methoxyimino-2-furyl ammonium acetate

A technology of ammonium furyl acetate and methoxyimino, which is applied in the field of drug synthesis, can solve the problems of low total reaction yield, adverse effects on the occupational health of operators and the environment, and cumbersome processes, and achieve high yield and purity. Effect

Active Publication Date: 2016-12-07
四平市精细化学品有限公司
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has the following disadvantages: 1, the process is loaded down with trivial details, with acetylfuran as raw material, it will go through 4 steps of reaction, and the total reaction yield is

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 2-methoxyimino-2-furyl ammonium acetate
  • Preparation method of 2-methoxyimino-2-furyl ammonium acetate
  • Preparation method of 2-methoxyimino-2-furyl ammonium acetate

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0032] The invention provides a kind of preparation method of 2-methoxyimino-2-furyl acetate ammonium salt, comprising:

[0033] 1) reacting the compound of formula (I) structure with methoxyamine salt to obtain a reaction solution containing the compound of formula (II),

[0034]

[0035] where the R 1 It is C1~C8 alkyl group;

[0036] 2) adding alkaline hydrolysis to the reaction solution containing the compound of formula (II) obtained in step 1), to obtain a reaction solution containing the compound of formula (III),

[0037]

[0038] 3) adding ammonia to the reaction solution containing the compound of formula (III) to form a salt to obtain ammonium salt of 2-methoxyimino-2-furyl acetate.

[0039] According to the present invention, the present invention reacts the compound of formula (I) structure with methoxyamine salt to obtain the reaction solution containing the compound of formula (II); wherein, the compound of formula (I) structure can be isolated single T...

Embodiment 1

[0048] 1) Add 136g (2.00mol) of furan, 500g of dichloromethane and 136g (1.0mol) of zinc dichloride into the reaction vessel. The reaction temperature was controlled at 10°C, and 382 g (2.8 mol) of methyl chlorooxalate was added dropwise. After the addition was completed, the reaction was continued for 6h. After the reaction was complete, the reaction mixture was added to water. Stirring, extraction and separation, the obtained organic phase containing 2-oxofuryl acetate was directly used for the next reaction.

[0049] 2) Add 414 g (3.0 mol) of potassium carbonate to the organic phase containing 2-oxofuryl acetate obtained in step 1). The temperature of the system was kept at 0° C., and 184 g (2.2 mol) of methoxyamine hydrochloride was slowly added for not less than 1 hour. After the addition was completed, the reaction was continued at 0°C for 8h. HPLC monitoring of trans by-products was less than 5%. After the reaction is finished, the solution system containing the pr...

Embodiment 2

[0054] 1) Add 136g (2.00mol) furan, 500g dichloroethane and 80g (0.6mol) aluminum trichloride to the reaction vessel, control the reaction temperature at 10°C, add dropwise 300g (2.2mol) ethyl chlorooxalate ester. After the addition was completed, the reaction was continued for 6h. After the reaction was complete, the reaction mixture was added to water. Stir, extract and separate. The obtained organic phase containing 2-oxofuryl acetate was directly used for the next reaction.

[0055] 2) Add 328 g (4.0 mol) of sodium acetate to the organic phase containing 2-oxofuryl acetate obtained in step 1). The temperature of the system was kept at 0° C., and 250 g (3.0 mol) of methoxyamine hydrochloride was slowly added for not less than 1 hour. After the addition was completed, the reaction was continued at 0°C for 8h. HPLC monitoring of trans by-products was less than 5%. After the reaction is finished, the solution system obtained containing the product cis-2-methoxyimino-2-fu...

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 provides a preparation method of 2-methoxyimino-2-furyl ammonium acetate. The preparation method includes: enabling a compound of a structure shown as a formula (I) to react with methoxyamine to obtain reaction liquid containing the compound of a structure shown as a formula (II); adding alkali into the reaction liquid to obtain reaction liquid containing a compound of a structure shown as a formula (III); adding ammonium salt into the reaction liquid containing the compound of the structure shown as the formula (III) to obtain 2-methoxyimino-2-furyl ammonium acetate. A target product is obtained by selecting the compound of the structure shown as the formula (I) as a starting raw material, enabling the starting raw material to react with methoxyamino acid and hydrolyzing and ammonifying a reaction product, preparation from the starting raw material to the final product can be completed in a same reaction system, an intermediate of the reaction does not need to be separated, and yield and purity of the reaction are high.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method of 2-methoxyimino-2-furyl acetate ammonium salt. Background technique [0002] Among the second-generation cephalosporin antibiotics, cefuroxime is actually the most produced and used antibiotic variety, and it has a huge consumer market and good development prospects. Therefore, as an essential intermediate in the preparation of cefuroxime, the preparation method of 2-methoxyimino-2-furyl acetamide ammonium salt has become the focus of attention of researchers in this field. [0003] Shi Lanxiang et al. reported in "Synthesis of cis-2-methoxyimino-2-furan acetic acid" that 2-furan carboxylic acid was used as the starting material, chlorination, cyanation, hydrolysis and oximation by thionyl chloride 2-Methoxyimino-2-furanacetic acid was synthesized. The cyanide reaction method was improved, and the total yield of 2-methoxyimino-2-furan acetic acid was 45.9%. ...

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): C07D307/54
CPCC07D307/54
Inventor 薛李冰刘长宝刘丽娟李永生王国慧李亚杰张宏
Owner 四平市精细化学品有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap