A kind of preparation method of 2,3-diaminopropionic acid methyl ester

A technology of methyl diaminopropionate and methyl serine, which is applied in the field of compound preparation, can solve problems such as cumbersome synthetic routes, mild reaction conditions, and difficulty in obtaining starting materials, and achieve high yield and mild reaction conditions.

Active Publication Date: 2021-07-30
NINGXIA MEDICAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these methods more or less have some deficiencies, such as the reaction conditions are not mild, the starting materials are difficult to obtain and the synthetic route is loaded down with trivial details etc.

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
  • A kind of preparation method of 2,3-diaminopropionic acid methyl ester
  • A kind of preparation method of 2,3-diaminopropionic acid methyl ester
  • A kind of preparation method of 2,3-diaminopropionic acid methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In this example, serine is used as a raw material, and the active ester generated by thionyl chloride and methanol is used in methanol to prepare serine methyl ester, which is then reacted with triphenylchloromethane to generate intermediate product 1, and the Trt group is introduced. Intermediate product 1 is Anhydrous tetrahydrofuran is solvent, in triphenylphosphine and diisopropyl azodicarboxylate DIAD (molecular formula is: (CH 3 ) 2 CHOOCN=NCOOCH(CH 3 ) 2 ) under the catalysis, react with phthalimide to generate intermediate product 2, introduce Pht group, intermediate product 2 removes Pht group to generate intermediate product 3 under the action of hydrazine hydrate, and finally intermediate product 3 is in hydrochloric acid ethanol Removal of the Trt group afforded the final product 4.

[0038] The specific process is as follows:

[0039] (1) Synthesis of serine methyl ester:

[0040] Add 30ml of methanol to a 100ml flask, stir in an ice-water bath, slowly...

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 method for preparing methyl 2,3-diaminopropionate, which uses serine as a raw material, uses thionyl chloride as a catalyst in methanol to prepare methyl serine, and then reacts with triphenylchloromethane to form Intermediate product 1, introduces Trt group, intermediate product 1 uses anhydrous tetrahydrofuran as solvent, under the catalysis of triphenylphosphine and DIAD, reacts with phthalimide to generate intermediate product 2, introduces Pht group, intermediate The Pht group of the product 2 was removed under the action of hydrazine hydrate to generate the intermediate product 3, and the Trt group of the final intermediate product 3 was removed in hydrochloric acid ethanol to obtain the final product 4.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to a preparation method of methyl 2,3-diaminopropionate. Background technique [0002] During the research and development of peptide inhibitors of cysteine ​​proteases, Pfizer synthesized a series of classic peptidomimetic inhibitors (the structure of which is shown in the structural formula), which are mainly used to inhibit the common cold and respiratory and intestinal diseases. Single-positive-sense RNA viruses that replicate for human diseases, such as human rhinovirus (HRV) in the picornavirus family and norwalk virus (NV) in the family Caliciviridae. Since the binding sites of human rhinovirus 3C protease (HRV 3CP) and Norwalk virus protease (NVPro) in these two viruses have a similar and highly conserved His-Cys-Glu catalytic triad for specific catalytic cleavage The Gln-Gly peptide bond is therefore considered a potential target protein. Most of the P1 seg...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/18C07C229/26
CPCC07C227/16C07C227/18C07D209/48C07C229/26C07C229/22
Inventor 黄宇王英樊艳茹
Owner NINGXIA MEDICAL UNIV
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