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

Synthetic method for chiral quaternary carbon oxazolidinone compound

A technology of carbooxazolinone and synthesis method, which is applied in the field of catalytic synthesis of chiral quaternary carbooxazolinone compounds, can solve the problems of low stereoselectivity, wide substrate range, complex catalyst, etc. Good selectivity, excellent corresponding selectivity, easy to purify

Inactive Publication Date: 2015-03-25
SUZHOU UNIV
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of various types of chemicals that can be used in industry or research purposes through specific reactions between different starting substances like hydroxylchloroquinalbonyl (HQ) binaphthoxyene-2-carboximide(BZO2) and 2-(methanesulfonylamino)-N'-(2-aminophenylethylenediaminetrimidinedithian-4)) mononucloradium salt complexes). These methods provide improved yields due to simplified operations while maintaining good stereoselective properties.

Problems solved by technology

The technical problem addressed by this patented technology relating to chemical reactions for producing various types of chirality-containing materials with unique properties that could potentially provide useful applications or improve their performance over time without causing negative health consequences. Existing techniques involve expensive starting material sources, complicated processes, difficult reaction conditions, limited choices between different configurations, and lacking flexibility towards changing structures during production process.

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
  • Synthetic method for chiral quaternary carbon oxazolidinone compound
  • Synthetic method for chiral quaternary carbon oxazolidinone compound
  • Synthetic method for chiral quaternary carbon oxazolidinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Add chiral quinine thiourea (2.8 mg, 0.005 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5a (5 mg), white solid, 10% yield, >20 / 1 dr, 30% ee.

[0029] Chiral quinine thiourea (5.6 mg, 0.01 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5a (27.2 mg), white solid, 55% yield, >20 / 1 dr, 70% ee.

[0030] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethy...

Embodiment 2

[0033]

[0034] Add chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5b (40.0 mg), white solid, 78% yield, >20 / 1 dr, 91% ee.

[0035]Add chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7 mg, 0.1 mmol), 3a (35.5 mg, 0.15 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5b (30.8 mg), white solid, 60% yield, >20 / 1 dr, 91% ee.

[0036] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7 mg, 0.1 mmol), 3a (23.7 mg, 0.1 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (elue...

Embodiment 3

[0039]

[0040] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2c (33.8 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5c (56.2 mg), white solid, 98% yield, >20 / 1 dr, 94% ee.

[0041] Add chiral quinine thiourea (11.2 mg, 0.02 mmol), and 2c (33.8 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol) sequentially into the reaction flask, add 1.5 mL m-xylene, and store at minus 30 degrees Celsius The reaction was carried out for 12 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5c (40.1 mg), white solid, 70% yield, >20 / 1 dr, 94% ee.

[0042] The product 5c was analyzed and the results are as follows: Determination by HPLC [Daicel Chiralcel AD-H, hexane / i-PrOH(70:30) , flow rate: 1.0 mL·min-1, ...

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 discloses a synthetic method for a chiral quaternary carbon oxazolidinone compound. The synthetic method comprises the following steps: taking o-hydroxy chalcone and azlactone as reactants and synthesizing in a solvent under the catalysis of chiral multifunctional chiral quinine thiourea to obtain a product. The synthetic method disclosed by the invention has the advantages that raw materials are easy to obtain, the reaction conditions are mild, the post-treatment is simple and convenient, the applicable substrate scope is wide, the yield is high, and the enantioselectivity is high; the product obtained by the synthesis method can be used for synthesizing an intermediate of a drug and a pesticide.

Description

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

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
Owner SUZHOU UNIV
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