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Method for fast synthesizing 3-substituted aromatic acid

A technique for the synthesis of aryl propionic acid, which is applied in chemical instruments and methods, preparation of carboxylic acid esters, preparation of organic compounds, etc., can solve problems such as difficult separation and purification, limited applicability, complicated post-treatment, etc., and achieves synthesis The effect of simple process, high cost of improvement, and simple purification and separation method

Inactive Publication Date: 2010-06-23
上海药明康德新药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to find a simple, convenient and economical new practical synthesis method of 3-substituted aryl propionic acid, which mainly solves the complex post-treatment, difficulty in separation and purification, low yield and high synthesis cost in the existing synthesis methods. Technical issues such as poor applicability

Method used

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  • Method for fast synthesizing 3-substituted aromatic acid
  • Method for fast synthesizing 3-substituted aromatic acid
  • Method for fast synthesizing 3-substituted aromatic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1 to 7

[0011]

[0012] Table 1: Synthesis of the corresponding 3-substituted phenylpropionic acid from substituted benzaldehyde

[0013]

[0014] a: separation yield b: HPLC purity

[0015] Typical reaction steps: add 2-methoxymethylbenzaldehyde (2g, 13.3mmol) and dimethylidene malonate (1.92g, 13.3mmol) to dry 5mL formic acid and 13mL triethylamine, reflux Stir for 10 hours; cool the reaction solution in an ice bath, add 20 mL of water, and then add 1M NaOH solution dropwise to adjust pH=9-10. The resulting solution was washed with ethyl acetate (2×20mL), the separated aqueous phase was added dropwise with 6M HCl solution to adjust the pH=2-4, extracted with ethyl acetate (2×50mL), the ethyl acetate phases were combined, and anhydrous sulfuric acid was added Sodium is dry. After filtration, the filtrate was concentrated under reduced pressure to obtain 3-(2'-methoxymethylphenyl)propionic acid.

[0016] 2a. Proton nuclear magnetic resonance spectroscopy 1 H NMR(CDCl 3 , 400MHz), δppm: 7....

Embodiment 8 to 11

[0030]

[0031] Table 2: Synthesis of the corresponding 3-substituted aromatic propionic acid from substituted aromatic formaldehyde

[0032]

[0033] a: separation yield b: HPLC purity

[0034] 4a. Proton nuclear magnetic resonance spectroscopy 1 H NMR(CDCl 3 , 400MHz), δppm: 7.96(d, J=8.0Hz, 1H), 7.55(t, J=7.2Hz, 1H), 7.43-7.38(m, 2H), 3.24(t, J=7.6Hz, 2H) , 2.80(t, J=7.6Hz, 2H)

[0035] HPLC purity: 98%; yield: 85%

[0036] 4b. Proton nuclear magnetic resonance spectroscopy 1 H NMR(DMSO-D 6 , 400MHz), δppm: 12.15 (brs, 1H), 7.42~7.33 (m, 1H), 7.23-7.19 (m, 2H), 2.79 (t, J = 7.6 Hz, 2H), 2.52 (t, J = 7.6 Hz, 2H)

[0037] HPLC purity: 97%; yield: 84%

[0038] 4c. Proton nuclear magnetic resonance spectroscopy 1 H NMR(CD 3 OD, 400MHz), δppm: 8.27-8.25 (dd, J 1 = 6.0 Hz, J 2 =1.2Hz, 1H), 8.19-8.17 (dd, J 1 =8.8Hz, J 2 =1.2Hz, 1H), 7.92-7.88 (dd, J 1 =8.8Hz, J 2 =5.6Hz, 1H), 4.08(s, 3H), 3.26(t, J=7.2Hz, 2H), 2.83(t, J=7.2Hz, 2H)

[0039] HPLC purity: 93%; yield: 72%

[0040] 4d. Proton nu...

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Abstract

The invention relates to a practical method for synthesizing 3-substituted aromatic acid, which not only solves the problems of the conventional method which has high cost, long reaction time, complicate aftertreatment and inconvenience for application operation, but also solves the problem that the conventional method is not applicable to a method for preparing 3-substituted aromatic acid by using aldehyde, the benzene rings of which have groups of nitryl, halogen and the like as raw materials. In the technical scheme, aromatic formaldehyde, dimethyl ethidine malonic ester are used as raw materials, reflux reaction is carried out in a mixed solvent of formic acid and saturated fatty amine, and then extraction by alkalization and acidification is performed for purification to directly obtain high-purification 3-substituted aromatic acid.

Description

Technical field: [0001] The invention relates to a rapid synthesis method of 3-substituted aromatic propionic acid, which can synthesize various 3-substituted aromatic propionic acids in large quantities through simple experimental means. Background technique: [0002] 3-Substituted arylpropionic acid compounds play an important role in the construction of small molecule drugs and are an important part of the molecular structure of many drugs, such as certain anti-AIDS drugs, non-steroidal anti-inflammatory drugs and psychiatric drugs. The structure of 3-substituted aromatic propionic acid, they all have good curative effect. [0003] The synthesis of 3-substituted aromatic propionic acid has the following reports: 1) Through cinnamaldehyde and RuCl 3 / Tricyclohexylphosphorus reaction or TMSCN / Lewis base synthesis; 2) Synthesis by the reaction of hydrogenated cinnamaldehyde and sodium nitrite; 3) Synthesis by iridium-catalyzed or biocatalytic reduction reaction of cinnamic acid; 4)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/64C07C69/767C07C67/30C07C205/56C07D213/65
Inventor 林文斌陈小珍王秋华肖贻崧郑吉富贺海鹰陈曙辉
Owner 上海药明康德新药开发有限公司
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