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3-Fmoc amino-3-(3-nitro-4-fluophenyl) propionic acid and preparation method thereof

A kind of technology of fluorophenyl and nitro group, applied in the field of 3-Fmoc amino-3-propionic acid and preparation thereof

Active Publication Date: 2011-03-16
合肥华纳生物医药科技有限公司
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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-Fmoc amino-3-(3-nitro-4-fluophenyl) propionic acid and preparation method thereof
  • 3-Fmoc amino-3-(3-nitro-4-fluophenyl) propionic acid and preparation method thereof
  • 3-Fmoc amino-3-(3-nitro-4-fluophenyl) 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 compound in the formula (I) and a preparation method thereof. The method comprises the following steps: 1) 4-fluorobenzaldehydes reacts to generate 3-nitro-4-fluophenyl fluorobenzaldehydes under the action of concentrated sulfuric acid and concentrated nitric acid; 2) the 3-nitro-4-fluophenyl fluorobenzaldehydes, malonic acid and ammonium acetate reflux in an alcohol solvent for 6 to 8 hours to prepare 3-amino-3-(3-nitro-4-fluophenyl) propionic acid; and 3) the 3-amino-3-(3-nitro-4-fluophenyl) propionic acid, a sodium carbonate solution with the weight percentage concentration of 8 to 12% and dioxane are mixed to form a suspension and the solution of Fmoc Cl or Fmoc-Osu and the dioxane is added in the suspension and reacts with the suspension to generate 3-Fmoc amino-3-(3-nitro-4-fluophenyl) propionic acid. The 3-Fmoc amino-3-(3-nitro-4-fluophenyl) propionic acid of the invention is combined with other amino acids to obtain a series of polypeptide compounds with certain inhibition activity on histone deacetylase (HDAC), and has the advantages of simple preparation method, easy obtainment of the raw materials, and high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 3-Fmoc 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 sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/22C07C269/04A61K31/27A61P3/10A61P35/02A61P29/00A61P37/06A61P33/02A61P37/00A61P35/00
Inventor 许峰高源
Owner 合肥华纳生物医药科技有限公司
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