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Bidentate Chiral Chromatographic Silanes and Chiral Stationary Phases Containing Tartrate Skeleton

A chiral and silane technology, applied in the field of chromatographic separation materials, can solve the problems of weak force of coating-type stationary phase, etc., achieve good chiral separation effect, simple synthesis method, and stable structure

Active Publication Date: 2016-01-13
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the force of the coating-type stationary phase is relatively weak, and chloroform, dichloromethane, ethyl acetate, and acetone cannot be used as mobile phases, and only alkanes and alcohols can be used as mobile phases

Method used

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  • Bidentate Chiral Chromatographic Silanes and Chiral Stationary Phases Containing Tartrate Skeleton
  • Bidentate Chiral Chromatographic Silanes and Chiral Stationary Phases Containing Tartrate Skeleton
  • Bidentate Chiral Chromatographic Silanes and Chiral Stationary Phases Containing Tartrate Skeleton

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Source of raw material 1

[0026] Dimethyl (+)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (M = 190) Alkaline hydrolysis to obtain (+)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dicarboxylic acid (M = 178).

[0027] Silane preparation

[0028] (1) Preparation of Intermediate 3

[0029] in N 2 Under protection, the raw material of 10.3g (50mmol) ( 1 ), 19.8g (110mmol) of raw material ( 2 ) was dissolved in 100ml of dichloromethane, continued stirring for 5-10 minutes, added 110mmol HBTU, 110mmol HOBT, 100ml DIEA, and stirred at room temperature for 2h. The reaction was detected by TLC point plate until the reactant ( 1 )disappear. The dichloromethane was removed by rotary evaporation, and the concentrate was added to refrigerated ether for precipitation, washed three times with refrigerated ether, and the intermediate ( 3 ). MS:m / z513.55[M+H] + . Elemental analysis: C%63.46; H%6.23; N%5.41.

[0030] (2) Preparation of Intermediate 4

[0031] ...

Embodiment 2

[0044] Silane preparation

[0045] (1) Preparation of Intermediate C

[0046] in N 2 Under protection, the raw material of 9.5g (40mmol) ( a) , 15g (84mmol) of raw material ( b) Dissolve in 100ml DMF, continue stirring for 5-10 minutes, add 84mmol HBTU, 84mmol HOBT, 50ml DIEA, and stir at room temperature for 2 hours. The reaction was detected by TLC point plate until the reactant ( a) disappear. The solvent was removed by rotary evaporation, the concentrate was precipitated by adding refrigerated ether, and washed three times with cold ether to obtain the intermediate ( c ). MS:m / z561.59[M+H] + . Elemental analysis: C%66.38; H%5.64; N%4.97.

[0047] (2) Preparation of intermediate d

[0048] Take by weighing 11.2g (20mmol) intermediate ( c ), add 100ml of 1N NaOH solution and 50ml of toluene, stir magnetically at 80°C for 2-3 hours, cool to room temperature, drop in 1N dilute hydrochloric acid to adjust the pH to neutral, evaporate to dryness under reduced pr...

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Abstract

The present invention discloses a bidentate chiral silane represented by general structural formula (I), wherein, R 1 and R 2 independently selected from C1-C30 alkyl, aryl, hydrogen, R 1 and R 2 not simultaneously hydrogen; R 3 C1~C30 alkyl, aryl substituted alkyl, cycloalkyl, aryl, heterocyclic; R 4 Is methyl or ethyl; n is an integer of 1-5. The stationary phase of the invention has better chiral separation effect, stable structure and convenient synthesis method.

Description

technical field [0001] The invention relates to a class of bidentate chiral chromatographic silane and chiral stationary phase containing tartaric acid skeleton, and belongs to the technical field of chromatographic separation materials. Background technique [0002] Many pharmaceuticals are chiral. The physical and chemical properties of chiral drug enantiomers are almost identical, only the optical activity is different, and there are great differences in physiological activity and pharmacological effects in vivo. Currently, many best-selling chiral drugs are single enantiomers, such as (S)-omeprazole, (S)-naproxen, (S)-propranolol, etc. Therefore, many countries stipulate that when reporting chiral drugs, the biological characteristics of the L-isomer and the D-isomer must be studied separately. It can be seen that efficient preparation methods of optically homochiral compounds and accurate determination of enantiomeric excess are becoming more and more important. [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J20/29
Inventor 贾艳艳孙晓莉李广庆贾玉晶
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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