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

(R)-TAPP-BINOL-COF polymer as well as preparation method and application thereof

A TAPP-BINOL-COF and -BINOL-CHO technology is applied in the direction of organic chemical methods, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., which can solve the problem of poor chiral selectivity and low yield. High production cost of clopidogrel and increase of wastes, etc., to achieve the effect of easy separation, low price, high yield and stereoselectivity

Active Publication Date: 2020-02-14
SHANDONG NORMAL UNIV
View PDF3 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many synthetic routes about clopidogrel reported at present, but the existing clopidogrel preparation technology generally has poor chiral selection, needs repeated chiral resolution, and problems such as low yield, which make the production of clopidogrel Increase in cost and waste

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
  • (R)-TAPP-BINOL-COF polymer as well as preparation method and application thereof
  • (R)-TAPP-BINOL-COF polymer as well as preparation method and application thereof
  • (R)-TAPP-BINOL-COF polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0051] Preferably, the preparation method includes: adding Cu-TAPP and (R)-BINOL-CHO to a mixed solution of dilute acetic acid, mesitylene and 1,4-dioxane for reaction.

[0052] Preferably, the reaction temperature is 110-130°C.

[0053] Preferably, the reaction time is 2.5-3.5d.

[0054] Preferably, the molar mass ratio of Cu-TAPP to (R)-BINOL-CHO is 0.8-1.2:1.8-2.2.

[0055] Preferably, the volume ratio of the dilute acetic acid, mesitylene and 1,4-dioxane is 2-4:4-6:14-17.

[0056] Preferably, the preparation method further includes: after the reaction is completed, collecting the solid part and washing with ethanol to obtain a purple-black powder, that is, the polymer (R)-TAPP-BINOL-COF.

[0057] The third aspect of the present disclosure provides the use of the polymer described in the first aspect as a catalyst.

[0058] Preferably, the catalyst is a clopidogrel intermediate catalyst; further, as (S)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c ]pyridin-5 (4H)-yl) a...

Embodiment 1

[0067] Embodiment 1: the synthesis of (R)-BINOL-CHO

[0068] Put R-1,1'-bi-2-naphthol (10.0mmol, 2.86g) in a 100ml three-necked flask, add dichloromethane (20ml), cool to 0°C, and slowly add liquid bromine ( 25.2mmol, 4.00 g), after the dropwise addition, the reaction solution was light orange. After continuing the reaction at 0°C for 24 h, add Na 2 S 2 o 3 (7.4 mmol, 1.20g) of aqueous solution, continue to stir for 2h. After the reaction was completed, the color of the reaction solution changed from orange to light yellow. Filter the reaction solution, transfer the filtrate to a separatory funnel, wash the organic phase three times with saturated NaCl solution, combine the organic phases, and add an appropriate amount of NaCl 2 SO 4 After drying, the solvent was removed by rotary evaporation to obtain (R)-6,6'-dibromo-1,1'-bi-2-naphthol as a light yellow solid product.

[0069] Weigh (R)-6,6'-dibromo-1,1'-bi-2-naphthol (10.0mmol, 4.44g) into a 100ml flask, add acetone ...

Embodiment 2

[0073] Example 2: Synthesis of (R)-TAPP-BINOL-COF

[0074] Cu-TAPP (0.05mmol, 36.60mg), (R)-BINOL-CHO (0.10mmol, 61.60 mg), dilute acetic acid (6M, 0.30ml) and 1,4-dioxane / mesitylene (2ml , volume ratio = 3:1) solution into the pressure tube. After freezing with liquid nitrogen, vacuumize, and then thaw, the above operation was repeated three times, and then placed in a 120°C constant temperature oven to react for 3 days. After cooling to room temperature, it was collected by centrifugation, washed repeatedly with ethanol, and vacuum-dried to obtain a purple-black Cu-COF powder with a yield of 82%.

[0075] In this embodiment, solid NMR, PXRD, N 2 The compound was characterized by adsorption and TGA, and the results are shown in figure 1 , 5 , 6 and 7. It can be seen that the polymer has a hollow structure. The ultraviolet absorption of (R)-TAPP-BINOL-COF prepared by the above method in acetonitrile solution ( image 3 ) shows that it has the maximum absorption at 420nm...

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 belongs to the technical field of COF catalysts, and particularly relates to a (R)-TAPP-BINOL-COF polymer as well as a preparation method and applications thereof. The invention providesa preparation method and applications of covalent organic framework (R)-TAPP-BINOL-COF. The (R)-TAPP-BINOL-COF is crystallized in a C2 space group. The catalyst can effectively catalyze a synthetic reaction of a clopidogrel intermediate through photothermal conversion under illumination conditions, is mild in reaction conditions, short in reaction time and less in catalyst dosage, can be repeatedly used for more than five times, and has good economic significance when being applied to industrial production.

Description

technical field [0001] The disclosure belongs to the technical field of COF catalysts, and in particular relates to a two-dimensional chiral (R)-TAPP-BINOL-COF polymer, its preparation method, and its application as a chiral drug clopidogrel precursor catalyst. Background technique [0002] The information disclosed in this Background section is only intended to increase the understanding of the general background of the disclosure, and is not necessarily to be taken as an acknowledgment or any form of suggestion that the information constitutes prior art that is already known to those skilled in the art. [0003] Covalent organic frameworks (COFs) are a class of crystalline porous materials, which consist of organic building units connected by covalent bonds into an ordered structure, forming a periodic porous COFs framework. COFs have the advantages of large specific surface area, light weight, and stable structure, and have good development prospects in the fields of cata...

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 Applications(China)
IPC IPC(8): C08G73/00B01J31/22C07D495/04
CPCC08G73/00B01J31/1691B01J31/183C07D495/04B01J2531/025B01J2531/16C07B2200/07
Inventor 董育斌马慧超陈功军
Owner SHANDONG NORMAL UNIV
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