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

Method for preparing caffeic acid derivative

A technology of derivatives and caffeic acid, applied in the field of preparation of caffeic acid derivatives, can solve the problem of no synthesis method and the like, and achieve the effects of low production cost, high product yield and short synthesis route

Active Publication Date: 2016-11-23
KPC PHARM INC
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, there is no information about two related derivatives of caffeic acid, 3-methoxy-4-difluoromethoxycinnamic acid and 3-cyclopropylideneoxy-4-difluoromethoxycinnamic acid. Literature reports on 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
  • Method for preparing caffeic acid derivative
  • Method for preparing caffeic acid derivative
  • Method for preparing caffeic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0018] The preparation method of the caffeic acid derivative of the present invention is to use the compound shown in the formula II as a raw material to undergo a substitution reaction with a halogenated alkane to obtain the compound shown in the formula III, and then carry out the Perkin reaction with acetic anhydride to obtain the compound shown in the formula I The compounds shown are the target caffeic acid derivatives, wherein the structures of the compounds shown in formula I, formula II and formula III are as follows:

[0019]

[0020] In the formula: R represents methyl or cyclopropyl methylene.

[0021] The substitution reaction is to dissolve the raw material and 3-hydroxy-4-difluoromethoxybenzaldehyde in an organic solvent, react at 50-85°C for 2-6 hours under the action of an alkali catalyst, filter the reaction solution, and filter the residue with di Wash and concentrate with methyl chloride, add water to the concentrated solution, extract with dichloromethan...

Embodiment 1

[0032] Example 1 Preparation of 3-cyclopropylideneoxy-4-difluoromethoxycinnamic acid

[0033] a. Preparation of intermediate 3-cyclopropylideneoxy-4-difluoromethoxybenzaldehyde

[0034] In a reaction flask, add 3-hydroxy-4-difluoromethoxybenzaldehyde (21g, 0.11mol), cyclopropylmethyl bromide (18.1g, 0.13mol), K 2 CO 3 (18.5g), dissolved in 199.5gDMF, reacted for 2h under stirring at 85°C. After TLC monitoring until the reaction is complete, filter the reaction solution, and use CH 2 Cl 2 Wash and concentrate, add CH to the concentrate 2 Cl 2 、H 2 O liquid extraction, take the organic phase with anhydrous MgSO 4 After drying and concentrating, 31 g of light yellow 3-cyclopropylideneoxy-4-(difluoromethoxy)benzaldehyde solution was obtained.

[0035] b. Preparation of 3-cyclopropylideneoxy-4-difluoromethoxycinnamic acid

[0036] In the reaction flask, add 3-cyclopropylideneoxy-4-difluoromethoxybenzaldehyde (2.41g, 0.01mol), acetic anhydride (3.06g, 0.03mol), K 2 CO 3 ...

Embodiment 2

[0039] Example 2 Preparation of 3-methoxy-4-difluoromethoxycinnamic acid

[0040] The preparation of the compound 3-methoxy-4-difluoromethoxycinnamic acid in this example refers to Example 1, and a white solid 3-methoxy-4-difluoromethoxycinnamic acid is prepared, the yield: 79 %.

[0041] The compound NMR identification is as follows:

[0042] 1H-NMR (500MHz, CDCl3, δppm): δ11 (s, 1H), δ6.70 (s, 1H), δ6.61 (m, 1H), δ6.75 (m, 1H), δ3.73 (s , 3H), δ7.36 (s, 1H), δ6.41 (d, 1H), δ7.61 (d, 1H). The structural formula is shown in Table 1.

[0043] Table 1 Compound structural formula that embodiment 1~2 makes

[0044] Example number Compound number R structural formula 1 KPC-3000179 2 KPC-3000180

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 discloses a method for preparing a caffeic acid derivative. A compound shown as the formula II serves as a raw material to be subjected to a substitution reaction with haloalkane to prepare a compound shown as the formula III, and the compound shown as the formula III and acetic anhydride are subjected to a Perkin reaction to prepare a compound shown as the formula I, namely, the target object caffeic acid derivative, wherein the structures of the compounds shown as the formula I, the formula II and the formula III are shown in the specification, wherein R represents methyl or cyclopropyl cyclopropyl. According to the method, the synthetic route is short, the product yield is high, adopted reagents are low in toxicity and safe, the production cost is low, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and in particular relates to a preparation method of caffeic acid derivatives. Background technique [0002] Caffeic acid, also known as 3,4-dihydroxycinnamic acid, has a molecular formula of C9H8O4, a molecular weight of 180.16, and a chemical structural formula of: [0003] [0004] caffeic acid [0005] Caffeic acid is widely found in the rhizomes or fruits of plants such as Compositae, Rosaceae, and Sapindaceae. Modern pharmacological studies have shown that caffeic acid has good antibacterial, detoxifying, and central excitatory effects. Another natural product - ferulic acid, also known as 3-methoxy-4-hydroxycinnamic acid, has a molecular formula of C10H10O4, a molecular weight of 194.19, and a chemical structural formula of: [0006] [0007] ferulic acid [0008] Ferulic acid is an effective component of Chinese medicinal materials such as angelica and c...

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): C07C59/64C07C59/72C07C51/353
CPCC07C45/64C07C47/575C07C51/353C07C59/64C07C59/72
Inventor 宋立明杨兆祥王贤李剑锋
Owner KPC PHARM INC
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