Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

3-Boc amidocyanogen-3-(3-nitryl-4-fluorophenyl) monoprop and preparation method thereof

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

Active Publication Date: 2012-08-22
合肥华纳生物医药科技有限公司
View PDF3 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 3-Boc amidocyanogen-3-(3-nitryl-4-fluorophenyl) monoprop and preparation method thereof
  • 3-Boc amidocyanogen-3-(3-nitryl-4-fluorophenyl) monoprop and preparation method thereof
  • 3-Boc amidocyanogen-3-(3-nitryl-4-fluorophenyl) monoprop 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a compound disclosed as a formula (I) and a preparation method thereof. The preparation method comprises the following steps of: (1) reacting 4-fluorobenzaldehyde to generate 3-nitryl-4-fluorobenzaldehyde under the actions of oil of vitriol and strong nitric acid; (2) refluxing the 3-nitryl-4-fluorobenzaldehyde, propane diacid and ammonium acetate for 6-8 hours in an alcoholic solvent to obtain 3-nitryl-3-(3-nitryl-4-fluorophenyl) monoprop; (3) mixing the 3-nitryl-3-(3-nitryl-4-fluorophenyl) monoprop, a sodium carbonate solution with mass percent concentration of 8-12 percent and dioxane to form suspending liquid, adding Boc2O and a dioxane solution into the suspending liquid, and reacting to generate the 3-Boc amidocyanogen-3-(3-nitryl-4-fluorophenyl) monoprop.The 3-Boc amidocyanogen-3-(3-nitryl-4-fluorophenyl) monoprop is synthesized with other amino acids to obtain a series of polypeptide compounds which have certain inhibitory activity with histone deacetylase (HDAC). The invention has simple preparation method and high yield, and raw materials are easy to obtain.

Description

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

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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 合肥华纳生物医药科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com