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Bidentate peptide chiral silane and chromatographic chiral stationary phase

A chiral chromatography and chirality technology, applied in the field of chromatographic separation materials, can solve the problems of short service life and weak acting force of the coated stationary phase, and achieve the effects of simple method, short synthesis route and good effect.

Active Publication Date: 2014-05-07
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the service life of coated stationary phases is short, and their force is relatively weak. Some solvents such as chloroform, dichloromethane, ethyl acetate, and acetone cannot be used as mobile phases, and only non-polar alkanes and alcohols can be used as mobile phases. mobile phase

Method used

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  • Bidentate peptide chiral silane and chromatographic chiral stationary phase
  • Bidentate peptide chiral silane and chromatographic chiral stationary phase
  • Bidentate peptide chiral silane and chromatographic chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Take 1,4-diphenol as raw material

[0035]

[0036] (1) Silica gel pretreatment

[0037] Kromasil Si-Tech spherical silica gel (pore size 100?, particle size 5.0 μm, specific surface area 340 m 2 / g, the metal impurity content is less than 30 ppm), according to the volume mass ratio of hydrochloric acid and silica gel 2 ml / g, mix hydrochloric acid with a volume percentage of 20% and silica gel, heat to 100°C and reflux for 4h. Filter with suction, wash with deionized water until neutral, wash with methanol, and dry at 160°C for 24h.

[0038] (2) Preparation of binaphthol-phenylalanine silane 5

[0039] ① Preparation of Intermediate 3: Weigh 8.5g (32mmol) of raw material (2) and put it into a three-neck bottle. Install a condenser tube and a dropping funnel, and feed dry nitrogen. Add 250ml of dry toluene and 8.0g of trifluoroacetic anhydride, and stir at room temperature until (2) is completely dissolved. Add 4.3g (15mmol) of raw material (1),...

Embodiment 2

[0053] Embodiment 2: Take 1,4-diphenol as raw material

[0054]

[0055]

[0056] (1) Preparation of binaphthol-dipolyphenylalanine silane 9

[0057] Preparation of Intermediate 7

[0058] Take 8.7g (15mmol) intermediate (4) and dissolve in 500ml dichloromethane, N 2 Stir under protection, then add 32mmol BOP, 32mmol HOBT, 10ml DIEA, continue stirring for 20 minutes, then add 8.5g (32mmol) raw material (2), and stir at room temperature for 2h. The reaction was detected by TLC spot plate until the raw material of the reactant disappeared. The reaction mixture was rotary evaporated to remove dichloromethane, the concentrate was added to chilled diethyl ether for precipitation, and washed three times with cold diethyl ether. The reactant intermediate (7) was purified by column chromatography, 12.9 g, with a yield of 80%.

[0059] MS: m / z 1076.25 [M+H] + , 962.04 [M-tBu+H] + . Elemental analysis: C% 73.92; H% 6.35; N% 5.42. 1 H NMR (CDCl 3 ): δ 1.26 (s, 18H); δ ...

Embodiment 3

[0070] Embodiment 3: Take 1,2-diol as raw material

[0071]

[0072] (1) Preparation of silane 15

[0073] Preparation of Intermediate 13

[0074] In the three-necked flask equipped with a condenser tube and a dropping funnel, dry nitrogen gas was introduced. Add 10.7g (32mmol) of raw material (2), 250ml of dry toluene, and 8.0g of trifluoroacetic anhydride, and stir at room temperature until (2) is completely dissolved. Add 3.2g (15mmol) of raw material (11) and stir at 40°C for 24h. Add 90ml of ethyl acetate to dilute, separate the layers, wash the ethyl acetate layer with 2N sodium hydroxide solution, hydrochloric acid and water twice, combine the organic phases, and dry over anhydrous sodium sulfate overnight. Filtration and removal of the solvent under reduced pressure gave a crude product, which was purified by flash column chromatography to obtain 11.0 g of solid intermediate (13) with a yield of 85%.

[0075] MS: m / z 708.33[M] + , 709.33 [M+H] + . Elemental...

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Abstract

The invention discloses bidentate peptide chiral silane as shown in a structural general formula (I). In the structural general formula, R1, R2 and R3 are alkyl group, naphthenic base, aromatic base and heterocyclic radical, n is an integer in the range of 1-10, alpha is 0, 1, 2, and X is halogen, alkoxy, acyloxy or amido. A synthesis method of the bidentate multichiral center bonding type chromatographic chiral stationary phase comprises the following steps: taking diol or diphenol as a raw material, combining ester bonds and peptides, finally introducing micromolecular silane, and synthesizing the bidentate multichiral center bonding type chromatographic chiral stationary phase. The chiral stationary phase has the characteristic of peptide chiral structure, meanwhile has the pi-pi effect of multiple aromatic rings and good chiral separation effect and is firmer than a unidentate bonding chiral stationary phase. The synthetic route is short, and the method is simple and convenient.

Description

technical field [0001] The invention relates to a new class of chiral chromatographic silane, chromatographic stationary phase and a synthesis method thereof, belonging to the technical field of chromatographic separation materials. Background technique [0002] Many biologically active compounds, such as pharmaceuticals and pesticides, are chiral. The pharmacological effects of chiral drugs are achieved through strict chiral recognition and matching with macromolecules in vivo. Although the physical and chemical properties of chiral enantiomers are almost identical, only the optical activity is different, and there are great differences in the physiological activity and pharmacological effects in vivo. For this reason, many countries stipulate that all information such as the physiological activity of optical isomers must be provided when reporting chiral drugs. Therefore, it is of great theoretical and practical significance to establish a high-specificity, high-sensitiv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/29B01J20/30
Inventor 文爱东李广庆孙晓莉贾艳艳贾玉晶
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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