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Preparation method of phenylalanine compound

A compound, the technology of propionic acid, which is applied in the field of preparation of phenylalanine compounds, can solve the problems of high impurity content, many side reactions, and inability to carry out large-scale industrial production, and achieve the effect of high purity

Active Publication Date: 2018-04-03
SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, this method has many side reactions, and the resulting product has many types of impurities and high impurity content, and the impurities in the product are difficult to remove by conventional treatment methods (including recrystallization), and it needs to be purified by chromatographic separation, which cannot be carried out on a large scale. Industrial production

Method used

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  • Preparation method of phenylalanine compound
  • Preparation method of phenylalanine compound
  • Preparation method of phenylalanine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propionic acid preparation

[0038]

[0039] Add 400mL toluene, 39.34g (100mmol) 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester, 43.40g (150mmol) 9-carbazole ethanol mesylate and 39.40g (120mmol) cesium carbonate were reacted at 90°C for 3 hours, filtered, and the filtrate was concentrated in vacuo to remove the solvent toluene to obtain 2-[(2-(4-fluorobenzene Formyl)phenyl)amino]-3-(4-hydroxyphenyl)propanoic acid methyl ester crude product, purity (HPLC) 69.8%, LC-MS (m / z) 587 (M+1). The obtained crude product was directly used in the next reaction without further purification.

[0040] Add the crude product of methyl 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propionate and 400 mL of tetrahydrofuran into the reaction flask, and stir to dissolve at room temperature. 16.78g (400mmol) LiOH.H2O was dissolved in 200mL of water, added...

Embodiment 2

[0041] Example 2: 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propionic acid preparation

[0042]

[0043] Add 40mL toluene, 3.93g (10mmol) 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester, 4.34g (15mmol) 9-carbazole ethanol mesylate and 3.95g (12mmol) cesium carbonate were reacted at 80°C for 2 hours, filtered, and the filtrate was concentrated in vacuo to remove the solvent toluene to obtain 2-[(2-(4-fluorobenzene Formyl)phenyl)amino]-3-(4-hydroxyphenyl)propanoic acid methyl ester crude product, LC-MS (m / z) 587 (M+1). The obtained crude product was directly used in the next reaction without further purification.

[0044] Add the crude 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propanoic acid methyl ester and 40mL tetrahydrofuran into the reaction flask, and stir at room temperature to dissolve. 1.68g (40mmol) LiOH.H2O was dissolved in 20mL of water, added to the above solution, stirred and rea...

Embodiment 3

[0045] Example 3: 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propionic acid preparation

[0046]

[0047] Add 40mL toluene, 3.93g (10mmol) 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester, 4.34g (15mmol) 9-carbazole ethanol mesylate and 3.95g (12mmol) cesium carbonate were reacted at 120°C for 2 hours, filtered, and the filtrate was concentrated in vacuo to remove the solvent toluene to obtain 2-[(2-(4-fluorobenzene Formyl)phenyl)amino]-3-(4-hydroxyphenyl)propanoic acid methyl ester crude product, LC-MS (m / z) 587 (M+1). The obtained crude product was directly used in the next reaction without further purification.

[0048] Add the crude 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl)propanoic acid methyl ester and 40mL tetrahydrofuran into the reaction flask, and stir at room temperature to dissolve. 1.68g (40mmol) LiOH.H2O was dissolved in 20mL of water, added to the above solution, stirred and ...

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Abstract

The invention discloses a preparation method of 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazole-9-yl)ethoxy)phenyl) propionic acid. The method comprises the step: carrying out condensation, hydrolysis and acidification on 9-carbazole ethyl alcohol methanesulfonate and 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-(4-hydroxyphenyl) methyl propionate serving as initial raw materials to obtain a target compound. The preparation method disclosed by the invention is suitable for industrial production, and the obtained target compound is high in purity.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of phenylalanine compounds. Background technique [0002] 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propanoic acid is a A phenylalanine compound with therapeutic and preventive activity for diseases, its chemical structural formula is as follows: [0003] [0004] The pharmacological activity of this compound is described in Chinese patent application CN03126974.5 and US patent application US7,268,157. 2-(2-(4-fluorobenzoyl)phenylamino)-3-(4-(2-(9H-carbazol-9-yl)ethoxy)phenyl)propionic acid selectively activates PPAR The ability of -α, PPAR-γ and PPAR-δ can be used to treat diseases related to metabolic syndrome, such as diabetes, hypertension, obesity, insulin resistance, hypertriglyceridemia, hyperglycemia, hypercholesterolemia, arterial Atherosclerosis, coronary heart disease, etc. [0005] 2-(2-(4-fluorobenzoyl)ph...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07C229/36
CPCC07C229/36C07D209/86
Inventor 鲁先平李志斌王祥辉
Owner SHENZHEN CHIPSCREEN BIOSCIENCES CO LTD
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