Beta-sulfonyl chiral amino compound and preparation method thereof

An amino compound and chiral technology, applied in the field of beta-sulfone-based chiral amino compounds and their preparation, to achieve the effects of shortening the reaction route, the reaction process being safe and controllable, and reducing the production cost

Inactive Publication Date: 2021-03-12
SHENZHEN BAY LAB PINGSHAN TRANSLATIONAL MEDICINE CENT
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of this application is to provide a β-sulfone-based chiral amino compound and its preparation method, aiming at solving the technical problem of how to provide more β-sulfone-based chiral amino compounds

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
  • Beta-sulfonyl chiral amino compound and preparation method thereof
  • Beta-sulfonyl chiral amino compound and preparation method thereof
  • Beta-sulfonyl chiral amino compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0071] On the other hand, on the basis of the β-sulfone-based chiral amino compound described above, the embodiment of the present application also provides a preparation method of the β-sulfone-based chiral amino compound of the general formula I above, Including the following steps:

[0072] S01: Provide nucleophile compound A and conjugated sulfone compound B represented by the following structural formula:

[0073]

[0074] S02: Add the nucleophile compound A and the conjugated sulfone compound B into a reaction system containing a nitrogen heterocyclic carbene catalyst and an alkaline reagent, and perform an asymmetric Michael addition reaction to obtain a general structural formula such as formula I The β-sulfone-based chiral amino compound shown.

[0075] FG in the above-mentioned nucleophile compound A molecular structural formula 1 and FG 2 The represented group is the same as FG in the β-sulfone chiral amino compound shown in the above formula I 1 and FG 2 Th...

Embodiment 1

[0090] This embodiment provides a kind of (R)-(benzyloxy)(1,1,1-trifluoro-3-(phenylsulfonyl)propan-2-yl)carbamate tert-butyl ester and its preparation method, which Structural formula is shown in following molecular structural formula I1:

[0091]

[0092] Its preparation steps are as follows:

[0093] In a dry 10mL test tube, add mesitylene-substituted indenol-derived triazolecarbene catalyst (0.02mmol, 0.2equiv.), 0.6mL anhydrous toluene, replace with argon three times, add base (0.02mmol, 0.2eq) to react The test tube was sealed and stirred at room temperature for 30 min. The nucleophile tert-butyl carbamate (0.12mmol, 1.2eq) was slowly added to the reaction system and stirred at room temperature for 0.5 hours. The corresponding β-trifluoromethyl unsaturated sulfone compound (0.1 mmol, 1.0 equiv.) was slowly added to the reaction system, and the resulting mixture was stirred at room temperature for 12 hours. After the reaction, the reaction solution was filtered throu...

Embodiment 2

[0096] This example provides a chiral (R)-(benzyloxy)(1,1,1-trifluoro-3-(pyridin-2-ylsulfonyl)propan-2-yl)carbamate tert-butyl ester And preparation method thereof, its structural formula is shown in following molecular structural formula I8:

[0097]

[0098] Its preparation steps are as follows:

[0099] In a dry 10mL test tube, add mesitylene-substituted indenol-derived triazolecarbene catalyst (0.02mmol, 0.2equiv.), 0.6mL anhydrous toluene, replace with argon three times, add base (0.02mmol, 0.2eq) to react The test tube was sealed and stirred at room temperature for 30 min. The nucleophile tert-butyl carbamate (0.12mmol, 1.2eq) was slowly added to the reaction system and stirred at room temperature for 0.5 hours. The corresponding β-trifluoromethyl unsaturated sulfone compound (0.1 mmol, 1.0 equiv.) was slowly added to the reaction system, and the resulting mixture was stirred at room temperature for 12 hours. After the reaction, the reaction solution was filtered t...

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 the technical field of organic synthetic chemistry, and particularly relates to a beta-carbonyl chiral amino compound and a preparation method thereof. The molecular structural general formula of the beta-sulfonyl chiral amino compound is shown in the formula I in the description, wherein different kinds of functional group substituents are introduced into R1, R2, FG1 andFG2 in the formula I, so that various types of beta-sulfonyl chiral amino compounds are achieved. In addition, the functional group on nitrogen in the formula I can be removed to become an exposed amino group. Therefore, a research basis is provided for screening useful molecules.

Description

technical field [0001] The application belongs to the technical field of organic synthesis chemistry, and in particular relates to a β-sulfone-based chiral amino compound and a preparation method thereof. Background technique [0002] The term "chirality" means that an object cannot coincide with its mirror image, such as our hands, the left hand does not coincide with the right hand which is a mirror image of each other. The term chirality is more commonly used in the field of chemistry and medicine. The chirality of molecules is usually caused by asymmetric carbons, that is, the four groups on one carbon are different from each other. Because a pair of molecules cannot overlap with each other like two human hands, they are called chiral compounds (chiral compounds), which refer to compounds with the same molecular weight and molecular structure, but opposite left and right arrangements (such as the real object and its mirror image). [0003] β-sulfone-based chiral amino c...

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): C07C317/32C07C315/04C07D213/71
CPCC07C317/32C07D213/71
Inventor 黄湧陈杰安郭芳芳
Owner SHENZHEN BAY LAB PINGSHAN TRANSLATIONAL MEDICINE CENT
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