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3-alloc amido-3-(3- nitryl-4-fluorophenyl) propionic acid and preparation method thereof

A technology of fluorophenyl and nitro, applied in the field of 3-Alloc amino-3-propionic acid and its preparation

Inactive Publication Date: 2012-08-22
BEIJING OKEANOS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For pharmaceutical companies, no one dares to ignore the role of unnatural amino acids in the development of new drugs

Method used

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  • 3-alloc amido-3-(3- nitryl-4-fluorophenyl) propionic acid and preparation method thereof
  • 3-alloc amido-3-(3- nitryl-4-fluorophenyl) propionic acid and preparation method thereof
  • 3-alloc amido-3-(3- nitryl-4-fluorophenyl) propionic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 18 grams of 4-fluorobenzaldehyde (15.6 milliliters, 0.145 moles, 1 equivalent, compound 4) was slowly added dropwise to 72 milliliters of concentrated sulfuric acid (commercially available concentrated sulfuric acid, concentration 98%) and 10.8 In the mixed solution of milliliter concentrated nitric acid (commercially available concentrated nitric acid, concentration is 68%). The dropping rate was 2 drops of 4-fluorobenzaldehyde / sec. After the dropwise addition, the reaction system was gradually raised to room temperature. After reacting at room temperature for 1 hour, the reaction system was poured into 450 g of ice cubes, and a large amount of solids were generated. After the ice cubes completely melted into water, the reaction system was filtered with suction to obtain a solid product. The aqueous phase was extracted twice with 250 ml of dichloromethane, and the solid product obtained by suction filtration was dissolved in 100 ml of dichloromethane. All organic ph...

Embodiment 2

[0040] 62 g of 4-fluorobenzaldehyde (53.7 ml, 0.5 mol, 1 equivalent, compound 4) was slowly added dropwise to a mixed solution of 186 ml of concentrated sulfuric acid and 18.6 ml of concentrated nitric acid at -5°C to 0°C. The dropping rate was 3 drops of 4-fluorobenzaldehyde / sec. After the dropwise addition, the reaction system was gradually raised to room temperature. After reacting at room temperature for 2 hours, the reaction system was poured into 1395 g of ice cubes, and a large amount of solids were generated. After the ice cubes completely melted into water, the reaction system was filtered with suction to obtain a solid product. The aqueous phase was extracted three times with 480 ml of ethyl acetate, and the solid product obtained by suction filtration was dissolved in 300 ml of ethyl acetate. All organic phases were combined, washed with saturated sodium bicarbonate solution until the pH value was 7-8, then washed with 350 ml of saturated brine, and then dried wit...

Embodiment 3

[0048] 93 g of 4-fluorobenzaldehyde (80.6 ml, 0.75 mol, 1 equivalent, compound 4) was slowly added dropwise to a mixed solution of 186 ml of concentrated sulfuric acid and 18.6 ml of concentrated nitric acid at -5°C to 0°C. The dropping rate was 4 drops of 4-fluorobenzaldehyde / sec. After the dropwise addition, the reaction system was gradually raised to room temperature. After reacting at room temperature for 2 hours, the reaction system was poured into 1860 g of ice cubes, and a large amount of solids were generated. After the ice cubes completely melted into water, the reaction system was filtered with suction to obtain a solid product. The aqueous phase was extracted twice with 826 ml of methyl tert-butyl ether, and the solid product obtained by suction filtration was dissolved in 400 ml of methyl tert-butyl ether. All organic phases were combined, washed with saturated sodium bicarbonate solution until the pH value was 7-8, then washed with 615 ml of saturated brine, and...

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Abstract

The invention relates to a 3-alloc amido-3-(3- nitryl-4-fluorophenyl) propionic acid and a preparation method thereof. The method comprises the following steps of: (1) generating 3-nitryl-4-fluorobenzaldehyde by reacting 4-fluorobenzaldehyde under the action of concentrated sulfuric acid and concentrated nitric acid; (2) refluxing the 3-nitryl-4-fluorobenzaldehyde, malonic acid and ammonium acetate in an alcoholic solvent for 6-8 h to obtain 3-amido-3-(3- nitryl-4-fluorophenyl) propionic acid; and (3) mixing the 3-amido-3-(3- nitryl-4-fluorophenyl) propionic acid with 8-12% sodium carbonate solution in percentage by weight and dioxane to form a suspension, adding a AllocCl and dioxane solution to the suspension and reacting to generate 3-alloc amido-3-(3- nitryl-4-fluorophenyl) propionic acid. A series of peptide compounds obtained by synthesizing the 3-alloc amido-3-(3-nitryl-4-fluorophenyl) propionic acid with other amino acids have a certain inhibitory activity on HDAC (Histone Deacetylase). The invention has the advantages of simple preparation method, easily obtained raw materials and high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 3-Alloc amino-3-(3-nitro-4-fluorophenyl) propionic acid and a preparation method thereof. Background technique [0002] Unnatural amino acids are amino acids encoded by non-protein genes, and have important applications in frontier biotechnology research such as genomics and proteomics. For example, α-unnatural amino acids are widely used in the study of proteins, nucleosides and nucleic acids: they can limit the conformational flexibility of polypeptides, provide deoxyribonucleic acid or ribonucleic acid molecules with stable secondary structure, enhance the ability of polypeptides to enzymes stability and improve pharmacokinetics and biological activity; β-unnatural amino acids are precursors of β-lactams and key components of many potential enzyme inhibitors, and have quite interesting pharmacological activities. β-unnatural amino acids have become more and more important s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/22C07C269/04C07K5/103A61K31/27A61P3/10A61P35/02A61P29/00A61P37/06A61P33/02A61P37/02A61P35/00
Inventor 许峰高源
Owner BEIJING OKEANOS TECH
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