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

Synthesis method of chiral epoxy compound and intermediate products and final product

A technology for epoxy compounds and synthesis methods, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of long routes and low resolution yields, achieve good industrial value, process optimization, and improve The effect of raw material utilization

Active Publication Date: 2010-04-07
ASYMCHEM LIFE SCI TIANJIN
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method of "patent application (CN200610129431)" has a long route, and the split yield is not high

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
  • Synthesis method of chiral epoxy compound and intermediate products and final product
  • Synthesis method of chiral epoxy compound and intermediate products and final product
  • Synthesis method of chiral epoxy compound and intermediate products and final product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Preparation of N-cyclopropyl-trans-2-hexenoamide Add 2.3kg of dichloromethane (15ml / g) and 114g of trans-2-hexenoic acid (1eq.) to a 5L reaction vessel, drop to the system Add 243g of N'N-carbonyldiimidazole (1.5eq.), after the dropwise addition, the system was refluxed for 4.5h; the temperature was lowered to 10°C, and 142g of cyclopropylamine (2.5eq.) was added dropwise. Incubate at 10±2°C for 12h. The organic phase was washed with an equal volume of 1.5 kg saturated brine, dried, filtered with suction, and the filtrate was spin-dried to obtain a crude product. The crude product was recrystallized with a mixed solvent of 1.7kg ethyl acetate and 216g cyclohexane, the ratio of the mixed solvent to the crude product was 15mL: 1g; wherein the volume ratio of ethyl acetate and cyclohexane was 8mL: 1mL to obtain a solid, the yield 76.8%.

[0040] 1HNMR (300MHz, CDCl3), δ0.501 (cyclopropyl CH2, m), δ0.772 (CH3, m), δ0.916 (CH2, m), δ1.460 (CH2, m), δ2.132 ( Cyclopropy...

Embodiment 2

[0052] (1) Preparation of N-cyclobutyl-trans-2-heptenamide

[0053] Add 3kg of dichloromethane (18ml / g) and 128g of trans-2-heptenoic acid (1eq.) to the 10L reaction vessel, add 356g of thionyl chloride (3eq.) dropwise to the system, after the addition is complete, the system is refluxed for 6h ; Cool to 10 ° C, dropwise added 213g cyclobutylamine (3eq.). Incubate at 10±4°C for 12h. The organic phase was washed with an equal volume of 2 kg saturated brine, dried, filtered with suction, and the filtrate was spin-dried to obtain a crude product. The crude product was recrystallized with a mixed solvent of ethyl acetate and cyclohexane (20 mL / g), wherein 2.5 kg of ethyl acetate and 277 g of cyclohexane were used to obtain a solid with a yield of 74.8%.

[0054] 1HNMR (300MHz, CDCl3), δ1.95 (cyclobutyl CH2, m), δ2.42 (cyclobutyl CH2, m), δ4.06 (cyclobutyl CH, m), δ0.94 (CH3, m ), δ1.33 (CH2, m), δ1.86 (CH2, m), δ6.08 (vinyl H, m), δ6.32 (vinyl H, m), δ8.34 (NH, m) .

[0055] ...

Embodiment 3

[0067] (1) Preparation of N-cyclohexyl-trans-2-octenamide

[0068] Add 2.2kg dichloroethane (12ml / g) in 5L reaction vessel, 142g trans-2-octenoic acid (1eq.), add dropwise 191g1-(3-dimethylaminopropyl)-3-ethane Carbodiimide hydrochloride (1eq.), the dropwise addition was completed, and the system was refluxed for 6h; the temperature was lowered to 10°C, and 149g of cyclohexylamine (1.5eq.) was added dropwise. Incubate at 10±2°C for 12h. The crude product was recrystallized from a mixed solvent of ethyl acetate and cyclohexane (12 mL / g), wherein 1.7 kg of ethyl acetate and 292 g of cyclohexane were used to obtain a solid with a yield of 72.1%.

[0069] 1HNMR (300MHz, CDCl3), δ1.52 (cyclohexyl CH2, m), δ1.39 (cyclohexyl CH2, m), δ1.68 (cyclohexyl CH2, m), δ3.28 (cyclohexyl CH, m) , δ0.94(CH3, m), δ1.33(CH2, m), δ1.86(CH2, m), δ6.52(vinyl H, m), δ6.26(vinyl H, m), δ8.18 (NH, m).

[0070] (2) Preparation of (2S, 3R)-N-cyclohexyl-2,3-epoxy-octylamide

[0071] a. Add 3.9kg tetr...

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a synthesis method of a chiral epoxy compound and intermediate products and a final product beta-amino acid derivative. The chiral epoxy compound is obtained by utilizing commercialized raw materials in markets as initial raw materials and then obtaining a chiral intermediate in the process of chemical reaction under mild conditions. In the method, the novel chiral catalyst method is utilized, a great amount of novel chiral catalyst ligand is synthesized by adopting the method in documents, epoxidation is carried out on olefin and then olefin is applied to the synthesis of the beta-amino acid derivative, thereby improving the use ratio of raw materials and optimizing the process from the origin. Epoxidation is carried out on unsaturated amide by the novel chiral ligand, and then open-loop deprotection is carried out to obtain the product. The value of product obtained by oxidation reaction is 80-99%, the yield coefficient thereof is 80-95%, and the chemical purity thereof is 90-99%, therefore, the chiral epoxy compound can be used for mass production and has very good industrial value.

Description

(1) Technical field [0001] The present invention relates to a kind of synthetic method of chiral epoxy compound and its intermediate product and final product β-amino acid derivative, it is through the raw material of commercialization on the market (trans, E configuration) as the initial raw material, after a mild chemical reaction process to obtain a chiral intermediate finally got (2) Technical background: [0002] Derivatives of β-amino acids can be introduced into peptide drugs to modify the structure of peptide chains and enhance their stability and activity in vivo; in addition, they can also be used as anti-tumor drugs, using amino acid derivatives as enzyme inhibitors to Treat tumors, or transform cancer cells into amino acid derivatives, so as to achieve the purpose of treating tumors. [0003] At this stage, the methods for preparing such compounds mainly include the following three categories: [0004] 1. Using α-amino acid as raw material, it can be obtai...

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 Applications(China)
IPC IPC(8): C07C231/12C07C237/06C07C233/09C07D303/48C07C237/04
Inventor 洪浩陈朝勇陈迥
Owner ASYMCHEM LIFE SCI TIANJIN
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