Polyethylene glycol-supported bis(S)-2-(4'-benzyloxy)-N-methyl ethane-1,2-diamine and preparation method and application thereof

A polyethylene glycol, methyl ethane technology, applied in the preparation of carboxylates, chemical instruments and methods, preparation of organic compounds, etc. Symmetric catalytic reaction is difficult to achieve large-scale industrial application and other problems, to achieve the effect of easy online detection, high stereoselectivity, and fast reaction

Inactive Publication Date: 2014-07-30
HUBEI UNIV
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, small molecular chiral catalysts are expensive and difficult to recycle and reuse, which has always been an obstacle to the large-scale industrial application of asymmetric catalytic reactions.

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
  • Polyethylene glycol-supported bis(S)-2-(4'-benzyloxy)-N-methyl ethane-1,2-diamine and preparation method and application thereof
  • Polyethylene glycol-supported bis(S)-2-(4'-benzyloxy)-N-methyl ethane-1,2-diamine and preparation method and application thereof
  • Polyethylene glycol-supported bis(S)-2-(4'-benzyloxy)-N-methyl ethane-1,2-diamine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-4

[0028] Example 1-4: Preparation method of polyethylene glycol-supported bis(S)-2-(4'-oxybenzyl)-N-methylethane-1,2-diamine.

[0029]

Embodiment 1

[0031] dry PEG 3400 (10.0 g, 5.8 mmol-OH) was dissolved in dry dichloromethane (100 mL), triethylamine (4.8 mL, 34.8 mmol) was added, and methylsulfonyl chloride was added dropwise at 0°C at 1 drop / second (1.4 mL, 17.4 mmol), react at 40°C for 6 h. The reaction solution was cooled to room temperature, washed with saturated NaCl solution (15 mL×3), anhydrous MgSO 4 Dry, filter, concentrate the filtrate, add anhydrous glacial ether (300 mL) to precipitate, filter, wash with glacial ether several times until TLC (ethyl acetate / petroleum ether=1 / 4, volume ratio) detects that there is no small molecule impurity in the product, The compound was dried under vacuum 2 (10.4 g, 99%). IR (NaCl): υ 2887, 1467, 1343, 1280, 1148, 1114, 963, 842 cm -1 ; 1 H NMR (600 MHz, CDCl 3 ): δ 3.77-3.53 (m, (OCH 2 CH 2 ) n ), 3.16-3.11 (m, 4H), 1.42 (t, J = 6.8 Hz, 6H); 13 C NMR (150 MHz, CDCl 3 ): δ 71.4-69.1, 46.1, 8.8.

[0032]

[0033]

Embodiment 2

[0035] compound 2 (10.0 g, 5.6 mmol) was dissolved in N, N-dimethylformamide (80 mL), and the compounds were added sequentially 3 Namely (S)-3-(4'-hydroxyphenyl)-N-methyl-2-(tert-butoxycarbonylamino)propionamide (3.31 g, 11.2mmol), Cs 2 CO 3 (3.67 g, 11.2 mmol) and 18-crown-6 (0.15 g, 0.56 mmol), react at 60°C for 12 h. N, N-dimethylformamide was distilled off under reduced pressure, the residue was dissolved in dichloromethane (100 mL), and the insoluble matter was filtered off. The filtrate was washed with saturated NaCl solution (15 mL×3), anhydrous MgSO 4 Dry, filter, concentrate the filtrate, add anhydrous glacial ether (300 mL) to precipitate, filter, wash with glacial ether several times until TLC (ethyl acetate / petroleum ether=1 / 4, volume ratio) detects that there is no small molecule impurity in the product, The compound was dried under vacuum 4 (10.0 g, 90 %). IR (NaCl): υ 3384, 3359, 2886, 1672, 1650, 1343, 1280, 1148, 1113, 963, 842 cm -1 ; 1 H NMR (400 M...

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 polyethylene glycol-supported bis(S)-2-(4'-benzyloxy)-N-methyl ethane-1,2-diamine and a preparation method and an application thereof. (S)-3-(4'-hydroxyphenyl)-N-methyl-2-(tertbutoxycarbonylamino)propionamide is supported on polyethylene glycol, then the prepared compound is used as a chiral catalyst for catalyzing an asymmetric reaction into a homogeneous reaction, the reaction is quick, and online detection is convenient. The chiral catalyst reagent not only retains high yield and high stereo selectivity of a diamine chiral catalyst in catalyzing the asymmetric reaction, the chiral compound having high optical purity is obtained, and at the same time, recycling and cycle use of the chiral catalyst is achieved. Furthermore, water which is non-toxic, cheap, abundant and environmentally friendly is used as a solvent in catalysis of a Michael-aldol tandem reaction, the economic and green chiral synthesis chemistry development trend is met, and the synthesized cyclohexanone compound with multiple chiral centers can be further derived into cyclohexanediol, gamma-lactone, epsilon-lactone and the like having optical activity and all used as precursors, intermediates and final products of medicines and functional materials.

Description

technical field [0001] The invention relates to a chiral catalyst polyethylene glycol supported bis(S)-2-(4'-oxybenzyl)-N-methylethane-1,2-diamine and its preparation method and application. Background technique [0002] Chiral compounds play an important role in the fields of fine chemicals, materials science, especially life science. The research on the synthesis method of chiral compounds not only has great scientific value, but also contains huge economic benefits. Asymmetric synthesis is the best way to prepare chiral compounds. It makes it possible to artificially design reaction conditions or substrates to control the attack direction of reagents or reaction sites to obtain optically pure isomers, which satisfies the needs of the chemical, biological and pharmaceutical industries. There is a strong demand for technologies for the synthesis of single-enantiomer chiral drugs. [0003] Asymmetric synthesis using a small amount of chiral catalysts is one of the most ef...

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): C08G65/48B01J31/06C07C69/757C07C51/373
CPCY02P20/584
Inventor 杨桂春陈祖兴卢翠芬聂俊琦潘小燕
Owner HUBEI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap