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Pre-column derivatization agent and its synthesis method

A synthetic method and compound technology, which is applied in the field of medicine, can solve the problems of insufficient rigor of chiral isomers, and achieve the effects of cheap raw materials, high yield, and increased content of finished products

Active Publication Date: 2012-10-17
WUHAN WUYAO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, ICH (International Council for Harmonization of Technical Requirements for Registration of Drugs for Human Use) has stricter requirements on the control of isomers of chiral drugs, and it is not rigorous enough to control the chiral isomers of chiral drugs by using specific rotation alone.

Method used

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  • Pre-column derivatization agent and its synthesis method
  • Pre-column derivatization agent and its synthesis method
  • Pre-column derivatization agent and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 The preparation of 2-chloro-3,5-dinitrobenzoyl chloride

[0028] Add 24.6 g of 2-chloro-3,5-dinitrobenzoic acid (100 mmol), 150 ml of thionyl chloride (2.0 mol) into a 500 ml single-necked flask, drop in 0.5 ml of DMF, stir magnetically, and heat up to 60-70°C , reacted for 5 to 6 hours, concentrated under reduced pressure to distill out thionyl chloride, and cooled to room temperature to obtain 25.8 g of a light yellow solid that was 2-chloro-3,5-dinitrobenzoyl chloride, with a yield of 97.4%.

Embodiment 2

[0029] Synthetic method one of embodiment 2 (S)-2-chloro-3,5-dinitro-N-(1-phenylethyl)benzamide

[0030] Take a solution of 0.48g (4mmol) S(-)-α-methylbenzylamine, 0.4g (4mmol) triethylamine dissolved in 5ml tetrahydrofuran, put it in an ice bath at 5-10°C, and add dropwise 1.06g (4mmol) 2 -Chloro-3,5-dinitrobenzoyl chloride was dissolved in 1ml of tetrahydrofuran and added dropwise. After the dropwise addition was completed, it was slowly raised to room temperature and reacted for 2 hours. After the reaction was detected by TLC, the reaction was stopped. The tetrahydrofuran was removed by rotary evaporation under reduced pressure, 10 ml of water and 10 ml of ethyl acetate were added for extraction, the aqueous layer was extracted once more with 10 ml of ethyl acetate, and the organic phases were combined. The organic phase was washed three times with 10% dilute hydrochloric acid aqueous solution, saturated sodium carbonate aqueous solution, and saturated sodium chloride aqueo...

Embodiment 3

[0032] The impact of adding different amounts of triethylamine on the production yield and quality of (S)-2-chloro-3,5-dinitro-N-(1-phenylethyl)benzamide: according to the preparation method one, The ratio of 2-chloro-3,5-dinitrobenzoyl chloride and triethylamine is selected to be 1:0.9, 1:0.7, 1:0.5, 1:0.3, 1:0.1 respectively, and 5 experiments are completed to obtain 5 samples, its yield, quality data are shown in the following table:

[0033]

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Abstract

The invention relates to a pre-column derivatization agent used for primary amine or secondary amine-containing chiral compounds detection and a synthetic method thereof, the chemical name of the derivatization agent I is (S)-2-chloro-3, 5-binitro-N-(1-phenethyl) benzamide, the synthesized derivatization agent is stable, and can be used for detecting the chiral compounds without ultraviolet absorption, and can replace a chiral column for detecting the chiral compounds with ultraviolet absorption.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a synthesis method and application of a pre-column derivatization reagent for chiral compounds containing primary or secondary amines, in particular to a chiral amine pre-column derivatization reagent (S)-2-chloro- Synthesis method and application of 3,5-dinitro-N-(1-phenylethyl)benzamide. Background technique [0002] With the increasing development of medicinal chemistry, there are more and more types of chiral compounds containing primary or secondary amines as drug intermediates and finished raw materials. Many of these chiral intermediates and finished raw materials containing primary or secondary amines Drugs have very weak UV absorption or are difficult to separate with ordinary C18 columns. How to effectively control the quality of these chiral compounds containing primary or secondary amines, it is extremely important to find a sensitive and efficient derivatization reagent with a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/65C07C231/02
Inventor 朱毅田俊峰潘继红郭亚兵杨尚金郭婷婷
Owner WUHAN WUYAO SCI & TECH