Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing O-tosyl-2-carbamoyl-2-methoxyl-imido-acetamido-oxime

A technology of methoxyiminoacetamide oxime and methoxyiminoacetamide, which is applied in the field of organic synthesis, can solve the problems of high production cost, low yield, harsh reaction conditions, etc., so as to reduce production cost, shorten the process flow, The effect of high yield

Active Publication Date: 2011-06-15
BENGBU BBCA MEDICINE SCI DEV
View PDF6 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because according to the preparation method of introducing methoxyimino after the preparation of cefzoram side chain acid route is lengthy, the reaction conditions are harsh, the yield is low, the production cost is very high, it is not suitable for industrialized production

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
  • Method for preparing O-tosyl-2-carbamoyl-2-methoxyl-imido-acetamido-oxime
  • Method for preparing O-tosyl-2-carbamoyl-2-methoxyl-imido-acetamido-oxime
  • Method for preparing O-tosyl-2-carbamoyl-2-methoxyl-imido-acetamido-oxime

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The first step: the preparation of intermediate 2-cyano-2-methoxyiminoacetamide (compound III)

[0031] Put 45g (0.53mol) of cyanoacetamide into a 500mL three-necked flask, 90mL of water, then drop in 36.6g (0.53mol) of sodium nitrite, control the temperature between 38-48°C, and then dropwise add sulfuric acid with a mass fraction of 62.5% 38g (0.23mol), stirred at the same temperature for 2-3h after the dropwise addition, TLC method monitoring reaction (developing agent is ethyl acetate: petroleum ether=5: 3) to the end, adding mass fraction is 40% sodium carbonate Adjust the pH of the reaction solution to 8.5-9.0, and add 67g (0.53mol) of dimethyl sulfate dropwise between 38-48°C with temperature control. After the dropwise addition, continue to stir for 3h, cool with ice water, filter the solid crystals, and use Wash with cold water and dry to obtain 50 g of 2-cyano-2-methoxyiminoacetamide, mp: 165-170°C. The liquid phase normalized content is 98.99%, and the yield...

Embodiment 2

[0033] The first step: the preparation of intermediate 2-cyano-2-methoxyiminoacetamide (compound III)

[0034] Put 45g (0.53mol) of cyanoacetamide into a 500mL three-necked flask, 90mL of water, then drop in 36.6g (0.53mol) of sodium nitrite, control the temperature between 38-48°C, and then dropwise add sulfuric acid with a mass fraction of 62.5% 50.0g (0.32mol), stirred at the same temperature for 2-3h after dropping, TLC method monitoring reaction (developing agent is ethyl acetate:petroleum ether=5:3) to the end, adding mass fraction is 10% hydrogen Sodium oxide solution, control the pH=7.5-8.5, control the temperature between 38-48°C, add 100.0g (0.79mol) of dimethyl sulfate dropwise, continue stirring for 3h after the dropwise addition, cool with ice water, and filter the solid crystal , washed with cold water and dried to obtain 45g of 2-cyano-2-methoxyiminoacetamide, mp: 165-170°C. The liquid phase normalized content is 98.5%, and the yield is 65.85%.

Embodiment 3

[0036] The second step: the preparation of O-tosyl-2-carbamoyl-2-methoxyiminoacetamide oxime (compound I)

[0037]Add 20g (0.16mol) 2-cyano-2-methoxyiminoacetamide, 12g (0.17mol) hydroxylamine hydrochloride, 160mL methanol to a 500mL three-necked flask, stir at room temperature, and slowly dropwise add 24mL (0.17 mol) triethylamine, stirred for about 5 hours after the addition, and the observation of the expansion plate showed that there was no raw material point (developing agent: methanol: petroleum ether = 5: 3), the reaction solution was cooled, and about 60mL of methanol was added, and 33.2g (0.17mol) p-toluenesulfonyl chloride, control the internal temperature below 5°C, add p-toluenesulfonyl chloride little by little, and drop 30mL (0.21mol) triethylamine at the same time, continue to Stir at high temperature for 1 hour, and the observation of the developing plate shows that there is no raw material point (developing agent is methanol:petroleum ether=5:3), then the reac...

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 method for preparing O-tosyl-2-carbamoyl-2-methoxyl-imido-acetamido-oxime, which comprises the following steps: (1) reacting cyanoacetamide, which is used as an initial raw material, with sodium nitrite in a nitrosation mode to obtain a reaction intermediate, and reacting the reaction intermediate with dimethyl sulfate in an esterification mode to obtain 2-cyano-2-methoxyl-imido-acetamide; and (2) under the action of hydroxylamine hydrochloride, hydrolyzing cyano groups in the 2-cyano-2-methoxyl-imido-acetamide obtained in the step (1) into amino groups, and reacting with p-methylbenzene sulfonyl chloride in an esterification mode to generate the O-tosyl-2-carbamoyl-2-methoxyl-imido-acetamido-oxime. The preparation method provided by the invention has the advantages of accessible raw materials, short technical process and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of organic synthesis, and relates to a method for synthesizing an important intermediate O-toluenesulfonyl-2-carbamoyl-2-methoxyiminoacetamide oxime which can be used for synthesizing the side-chain acid of cefozopram. Background technique [0002] In recent years, with the improvement of people's living standards, people pay more and more attention to their health. The average life expectancy of human beings around the world is gradually increasing. In our country, the average life expectancy of people has reached 72 years in 2008. The trend of increasing life expectancy will continue, and the reason for such a good result ultimately depends on the improvement of our country's medical level. A large part of the improvement of medical level comes from the development of antibiotic drugs. By 2008, the development of antibiotics had made considerable progress, and the fourth-generation antibiotics cefixitine and cefa...

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): C07C309/73C07C303/28
Inventor 徐景侠韦亚锋
Owner BENGBU BBCA MEDICINE SCI DEV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com