Method for preparing (R)-2, 3-diaryl substituted methyl propionate compound

A technology for methyl propionate and compounds, which is applied in the field of preparation of -2,3-diaryl substituted methyl propionate compounds, can solve problems such as difficulties, expensive catalysts and chiral resolution, and achieve low catalyst consumption , good yield and enantioselectivity, and the effect of reducing costs

Pending Publication Date: 2022-05-06
XINXIANG UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process involves useing cheap metal catalysis without adding expensive chemicals or requiring complicated processes for making certain types of molecules that could also function like those described earlier. It allows for easy access to these starting material while still producing high yield rates and specificity towards desired product(s). Additionally, it reduces costs by reducing the amounts needed compared to previous methods due to its simplicity.

Problems solved by technology

This patented technical problem addressed in this patents relates to improving methods used for producing specific chemicals called toletron or proton pump inhibitors that can treat certain medical conditions like urinary tract disorders caused by excessively active neurotransmitters. These compounds have potential use in medicine due their ability to block calcium channels involved with painful inflammatory processes associated therewith.

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
  • Method for preparing (R)-2, 3-diaryl substituted methyl propionate compound
  • Method for preparing (R)-2, 3-diaryl substituted methyl propionate compound
  • Method for preparing (R)-2, 3-diaryl substituted methyl propionate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation method of (R)-2,3-diaryl substituted methyl propionate compound, specifically comprises the following steps:

[0028] In a dry 15mL pressure-resistant reaction tube, add 103mg of 2-methoxy-4-methyl-cinnamic acid methyl ester (CAS: 86761-35-5), 78mg of phenylboronic acid, 2.0mg of cuprous chloride, 7.8mg P, N-type chiral ligand, 138mg potassium carbonate and 2.5ml tetrahydrofuran. The reaction was stirred at 50°C for 2 hours under nitrogen. After the reaction was completed, it was cooled to room temperature and directly passed through a silica gel column (volume ratio of petroleum ether to ethyl acetate was 15:1) to obtain 108 mg of product with a yield of 76% and ee of 89%. The reaction process is shown in the following formula:

[0029]

[0030] Carry out nuclear magnetic resonance and mass spectrometry to the product prepared in this embodiment:

[0031] 1 H NMR (400MHz, CDCl 3 ): δ=7.40(t, J=7.6Hz, 2H), 7.29(d, J=7.6Hz, 2H), 7.27(d, J=7.6Hz, 1H...

Embodiment 2

[0035] The preparation method of (R)-2,3-diaryl substituted methyl propionate compound, specifically comprises the following steps:

[0036] In a dry 15mL pressure-resistant reaction tube, add 103mg of 2-methoxy-4-methyl-cinnamic acid methyl ester (CAS: 86761-35-5), 97mg of phenylboronic acid, and 2.0mg of cuprous chloride, 7.8mg P, N-type chiral ligand, 138mg potassium carbonate and 2.5ml tetrahydrofuran. The reaction was stirred at 50°C for 2 hours under nitrogen. After the reaction was completed, it was cooled to room temperature, and directly passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 15:1), and 114 mg of the product was obtained, with a yield of 73%, and ee of 91%. The reaction process is shown in the following formula:

[0037]

[0038] Carry out nuclear magnetic resonance and mass spectrometry to the product prepared in this embodiment:

[0039] 1 H NMR (400MHz, CDCl 3 ): δ=7.38(t, J=7.6Hz, 2H), 7.31(d, J=7.6Hz, 2...

Embodiment 3

[0043] The preparation method of (R)-2,3-diaryl substituted methyl propionate compound, specifically comprises the following steps:

[0044] In a dry 15mL pressure-resistant reaction tube, add 103mg of 2-methoxy-4-methyl-cinnamic acid methyl ester (CAS: 86761-35-5), 93mg of 4-fluorophenylboronic acid, 2.0mg of chloride Cuprous, 7.8mg P, N-type chiral ligand, 138mg potassium carbonate and 2.5ml tetrahydrofuran. The reaction was stirred at 50°C for 2 hours under nitrogen. After the reaction was completed, it was cooled to room temperature, and directly passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 15:1), and 106 mg of product was obtained, with a yield of 70%, and ee of 89%. The reaction process is shown in the following formula:

[0045]

[0046] Carry out nuclear magnetic resonance and mass spectrometry analysis to the product prepared in this embodiment:

[0047] 1 H NMR (400MHz, CDCl 3): δ=7.43(t, J=7.6Hz, 2H), 7.37(d, J=...

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 method for preparing an (R)-2, 3-diaryl substituted methyl propionate compound, the (R)-2, 3-diaryl substituted methyl propionate compound is synthesized in one step by utilizing a cheap copper catalyst and the catalytic action of a P, N-type chiral ligand, the raw materials are easy to obtain, the preparation method is simple, and the yield and enantioselectivity are good; meanwhile, the catalyst dosage is small, and the cost can be greatly reduced. The method can be used for synthesizing a key intermediate of the medicine tolterodine for treating overactive bladder.

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 XINXIANG 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