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

Synthesis methods of deuterine, hippuric acid-L-menthol ester (2,2-D2) and intermediates thereof

A 2-D2, synthetic method technology, applied in the direction of organic chemical methods, chemical instruments and methods, carboxylic acid amide preparation, etc., can solve the problems of harsh reaction conditions, strict equipment requirements, unfavorable preparation, etc., and achieve easy access to raw materials, equipment Corrosion reduction, easy to scale up the effect of preparation

Pending Publication Date: 2018-08-03
CHANGSHA BEITA PHARMATECH CO LTD
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In summary, the current synthesis of glycine (2,2-D 2 ) method has higher cost, or strict requirements on equipment, or harsh reaction conditions, which are not conducive to large-scale preparation

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 methods of deuterine, hippuric acid-L-menthol ester (2,2-D2) and intermediates thereof
  • Synthesis methods of deuterine, hippuric acid-L-menthol ester (2,2-D2) and intermediates thereof
  • Synthesis methods of deuterine, hippuric acid-L-menthol ester (2,2-D2) and intermediates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] After successively adding 1.0 g of glycine and 100 mg of pyridoxal hydrochloride into the single-mouth bottle, the oil pump was replaced three times under the protection of argon, and then 10 mL of 10% (mass percentage) deuterium deuterium oxide aqueous solution was added under an argon atmosphere, and the reaction was refluxed for 2 hours. . After the reaction is finished, cool, (filter with a needle filter), spin out about 50% of deuterium water in a vacuum to recover, add 10 mL of distilled water after cooling, add 2.2 mL of benzoyl chloride, stir at room temperature overnight, then add crude ice, use Concentrated hydrochloric acid was used to adjust the pH value of the reaction solution to 2-3. After cooling, a large amount of solids were precipitated, filtered, and the filter cake was washed with ice water. Filter cake is recrystallized with hot water again, separates out white crystal, filters and dries, obtains 2.2g hippuric acid (2,2-D 2 ) pure product, yield 9...

Embodiment 2

[0058] After adding 1.0g of glycine, 100mg of pyridoxal hydrochloride, and 420mg of lithium metal in the three-neck flask, the oil pump was replaced three times under the protection of argon. After the reaction of lithium and deuterium water was complete, the temperature was raised to reflux for 2.5 hours. After the reaction is finished, cool, (filter with a needle filter), spin out about 50% of deuterium water in a vacuum to recover, add 10 mL of distilled water after cooling, add 2.2 mL of benzoyl chloride, stir at room temperature overnight, then add crude ice, use Concentrated hydrochloric acid was used to adjust the pH value of the reaction solution to 2-3. After cooling, a large amount of solids were precipitated, filtered, and the filter cake was washed with ice water. Filter cake is recrystallized with hot water again, separates out white crystal, filters and dries, obtains 2.0g hippuric acid (2,2-D 2 ) pure product, yield 82.9%, product purity>99% (HPLC), LC-MS and ...

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 synthesis methods of deuterine, hippuric acid-L-menthol ester (2,2-D2) and intermediates thereof, wherein the synthesis method includes the steps: (1) carrying out a reaction of glycine with a deuterium aqueous solution of alkali metal deuterium oxide under the action of pyridoxal or salts thereof, to obtain a deuterated reaction solution; and (2) recycling a part of deuterium water from the deuterated reaction solution obtained in the step (1) through reduced pressure distillation, then adding water and benzoyl chloride, carrying out an amidation reaction, and after the end of the reaction, posttreating to obtain hippuric acid (2,2-D2). The raw materials and reagents used in the synthesis method are cheap and easy to obtain, and the operation is simple; the purityand the deuterium abundance of the obtained deuterated reagents are high.

Description

technical field [0001] The invention belongs to the field of preparation of deuterated reagents, in particular to a synthetic glycine (2,2-D 2 ) and glycine (2,2-D 2 ) method for synthesizing a kind of α-deuterated amino acid module (hippuric acid-L-menthyl ester), especially relates to a kind of method directly using cheap glycine, deuterium water or sodium deuterium oxide etc. as raw materials to synthesize glycine (2,2-D 2 ) method, and glycine (2,2-D 2 ) is a method for further synthesizing an α-deuterated amino acid module (hippuric acid-L-menthyl ester) as a raw material. Background technique [0002] Glycine (2,2-D 2 ) is an important stable isotope-labeled amino acid, which has a wide range of applications in biomedicine, peptide research, protein metabolism and other biological and chemical aspects. Glycine (2,2-D 2 ) can be used to synthesize a variety of stable isotope-labeled polypeptide compounds, and it is also the synthetic precursor of amino acids used i...

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): C07C231/02C07C233/83C07C227/20C07C229/08C07C231/14C07B59/00C07C227/16
CPCC07B59/001C07C227/16C07C227/20C07C231/02C07C231/14C07C2601/14C07B2200/05C07C233/83C07C229/08Y02P20/584
Inventor 蔡定龙张雄伍君李刚
Owner CHANGSHA BEITA PHARMATECH CO LTD
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