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
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  • 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

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  • Method for preparing caffeic acid derivative
  • Method for preparing caffeic acid derivative
  • Method for preparing caffeic acid derivative

Examples

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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

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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

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Application Information

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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
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