Check patentability & draft patents in minutes with Patsnap Eureka AI!

Preparation method of O-methyl-threonine/tyrosine

A technology of tyrosine and threonine, which is applied in the field of preparation of threonine/tyrosine derivatives, can solve the problems of dangerous raw materials, long steps, unfriendly environment, etc., and achieve the effect of reliable operability and short reaction steps

Inactive Publication Date: 2018-05-08
滨海吉尔多肽有限公司
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a preparation method of O-methyl-threo / tyrosine, which mainly solves the problems of dangerous raw materials, unfriendly environment and long steps in the existing synthetic methods

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 O-methyl-threonine/tyrosine
  • Preparation method of O-methyl-threonine/tyrosine
  • Preparation method of O-methyl-threonine/tyrosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add N-tert-butoxycarbonyl-L-threonine into acetone, after all dissolve, keep the reaction system at 20-35°C, add 8 equivalents of sodium hydroxide in batches, stir for 2 hours after the addition, keep the reaction system at 0 -20°C, add 4 equivalents of dimethyl sulfate dropwise, react overnight at room temperature (20-30°C) after addition, add water to the reaction system, evaporate acetone at 40-50°C, after removing acetone, add Ethyl acetate and crushed ice, acidified with solid citric acid to pH=2-3, separated layers, discarded the water phase, washed the oil phase with saturated brine three times, dried over sodium sulfate for 2 hours, filtered to remove sodium sulfate, evaporated Part of ethyl acetate was added with petroleum ether and stirred for crystallization to obtain N-tert-butoxycarbonyl-O-methyl-L-threonine with a yield of 61%. Dissolve N-tert-butoxycarbonyl-O-methyl-L-threonine in acetone, keep at 10-25°C, add 4 equivalents of p-toluenesulfonic acid in ba...

Embodiment 2

[0018] Add N-tert-butoxycarbonyl-D-threonine into acetone, after all dissolve, keep the reaction system at 20-35°C, add 8 equivalents of sodium hydroxide in batches, stir for 2 hours after the addition, keep the reaction system at 0 -20°C, add 4 equivalents of dimethyl sulfate dropwise, react overnight at room temperature (20-30°C) after addition, add water to the reaction system, evaporate acetone at 40-50°C, after removing acetone, add Ethyl acetate and crushed ice, acidified with solid citric acid to pH=2-3, separated layers, discarded the water phase, washed the oil phase with saturated brine three times, dried over sodium sulfate for 2 hours, filtered to remove sodium sulfate, evaporated Part of ethyl acetate was added with petroleum ether and stirred for crystallization to obtain N-tert-butoxycarbonyl-O-methyl-D-threonine with a yield of 58%. Dissolve N-tert-butoxycarbonyl-O-methyl-D-threonine in acetone, keep at 10-25°C, add an equivalent amount of trifluoroacetic acid ...

Embodiment 3

[0020] Add N-tert-butoxycarbonyl-DL-threonine into acetone, after all dissolved, keep the reaction system at 20-35°C, add 8 equivalents of sodium hydroxide in batches, stir for 2 hours after the addition, keep the reaction system at 0 -20°C, add 4 equivalents of dimethyl sulfate dropwise, react overnight at room temperature (20-30°C) after addition, add water to the reaction system, evaporate acetone at 40-50°C, after removing acetone, add Ethyl acetate and crushed ice, acidified with solid citric acid to pH=2-3, separated layers, discarded the water phase, washed the oil phase with saturated brine three times, dried over sodium sulfate for 2 hours, filtered to remove sodium sulfate, evaporated Part of ethyl acetate was added with petroleum ether and stirred to crystallize to obtain N-tert-butoxycarbonyl-O-methyl-DL-threonine with a yield of 63%. N-tert-butoxycarbonyl-O-methyl-DL-threonine was dissolved in acetone, kept at 10-25°C, added 4 equivalents of p-toluenesulfonic acid...

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 O-methyl-threonine / tyrosine. The preparation method mainly overcomes the disadvantages of the existing method that a toxic reagent is volatile, the reagent is dangerous, the steps are long, the yield is low, and the like. The preparation method of the O-methyl-threonine / tyrosine comprises the following steps: N-t-butyloxycarboryl-threonine / tyrosineis catalyzed by sodium hydroxide and reacts with dimethyl sulfate to generate N-t-butyloxycarboryl-O-methyl-threonine / tyrosine, and then t-butyloxycarboryl is removed from the N-t-butyloxycarboryl-O-methyl-threonine / tyrosine through acid substances to obtain the product O-methyl-threonine / tyrosine. The product has important application in the fields of antibiotics and polypeptide drugs.

Description

technical field [0001] The invention relates to a preparation method of threo / tyrosine derivatives, especially a preparation method of O-methyl-threo / tyrosine. Background technique [0002] In the study of peptides and biologically active molecules, O-methyl-threo / tyrosine is a very meaningful building block. O-methyl-L-threonine can inhibit protein synthesis in Ehrlich ascites tumor cells. After modifying the internal structure of isopenicillin N with O-methyl-D-threonine, it becomes a new molecule, which has certain specific antibody activities. In the synthesis of new jodomycins, O-methyl-L-threo / tyrosine fragments can also be added to form brand new jodomycin derivatives for biological research. In short, O-methyl-threo / tyrosine is widely used in biopharmaceuticals and pharmacology. There are currently two mainstream synthetic methods: [0003] Journal of Organic Chemistry (1979 , vol. 44, p. 2299 – 2300) "Direct methylation of N-(tert-butoxycarbonyl)-O-methyl-L-seri...

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): C07C227/20C07C229/22C07C229/36
CPCC07B2200/07C07C227/20C07C269/06C07C229/36C07C229/22C07C271/22
Inventor 徐红岩奚文波周志国秦丽星
Owner 滨海吉尔多肽有限公司
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