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Bonded chiral amino alcohol polymer and preparation method and application thereof

A chiral amino alcohol and polymer technology, which is applied in the preparation of organic compounds, the preparation of carboxylic acid amides, chemical instruments and methods, etc., can solve the problems of easy loss of bonding rate of chiral selectors, and achieve strong chiral recognition ability. , to avoid loss, the effect of good physical and chemical stability

Inactive Publication Date: 2016-04-20
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Aiming at the defects that the existing commercialized chiral resolution materials are limited by the mobile phase, the chiral selector is easy to lose and the bonding rate is low when used as the chiral stationary phase, the purpose of the present invention is to provide a high-efficiency chiral Resolution ability, and good resistance to organic solvents, can avoid the loss of chiral selectors, a new type of bonded chiral amino alcohol polymer chiral resolution polymer material

Method used

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  • Bonded chiral amino alcohol polymer and preparation method and application thereof
  • Bonded chiral amino alcohol polymer and preparation method and application thereof
  • Bonded chiral amino alcohol polymer and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0064] Preparation of chiral monomer: Add 485mL of dry methanol into a 1000mL round bottom flask, suspend 30g (0.2287mol) L-leucine in anhydrous methanol, and dissolve excess SOC1 2 (80mL, 1.102mol) was added dropwise to the anhydrous methanol suspension, and the drop was completed within 30min, and then transferred to room temperature and stirred for 40h. The solvent was spun off, a certain amount of methanol was added and the solvent was spun dry to remove the generated hydrogen chloride and excess thionyl chloride to obtain white needle-like solid L-leucine methyl ester hydrochloride. At 30°C, add 200 mL of anhydrous tetrahydrofuran and magnesium chips (26.02 g, 1.0842 mol) into a 1000 mL three-necked flask, install a condenser tube and a dropping funnel containing 114 mL of bromobenzene and 50 mL of tetrahydrofuran, and put 2 mL of The anhydrous tetrahydrofuran solution of bromobenzene (0.06mol) is slowly dropped into the reaction system, and then a small amount of iodine ...

Embodiment 2

[0069] Preparation of chiral monomer: under ice-water bath cooling, excess SOC1 2 (0.225mol) was added dropwise to 150mL of L-leucine (0.075mol) methanol suspension, the drop was completed within 30min, and then transferred to room temperature and stirred for 24h. The solvent was spun off, a certain amount of methanol was added and the solvent was spun dry to remove the generated hydrogen chloride to obtain 13.3 g of L-leucine methyl ester hydrochloride as a white needle-like solid. At 30°C, add 50 mL of anhydrous diethyl ether and magnesium chips (0.06 mol) into a 100 mL three-necked flask, install a condenser tube and a dropping funnel, and add 2 mL of a diethyl ether solution of bromobenzene (0.06 mol) dropwise to the reaction system. Add iodine to initiate the reaction. After the color of iodine disappears, that is, after the reaction is initiated, slowly add the remaining ether solution of bromobenzene to keep the reaction stable and slightly boiling. The dripping is comp...

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Abstract

The invention discloses a bonded chiral amino alcohol polymer and a preparation method and application thereof. The bonded chiral amino alcohol polymer is composed of chiral amino acid derivative monomers on modified silica gel by virtue of amide group bonding. The preparation method comprises the following steps: taking L-amino acid as a raw material, and sequentially performing methyl esterification and phenylmagnesium bromide addition; introducing double bonds through acryloyl chloride, thereby obtaining a chiral monomer; polymerizing the chiral monomer and modified silica gel introduced with double bonds through free radicals, thereby obtaining the product. The process is simple in method, wide in raw material source and low in cost and is beneficial to industrial production; and moreover, the bonded chiral amino alcohol polymer has organic solvent resistance and high chiral resolution performance, can serve as a novel HPLC chiral stationary phase material applied to chiral compound identification or resolution and overcomes the defect that the existing chiral resolution material is limited by mobile phase.

Description

technical field [0001] The invention relates to a chiral polymer material for chiral resolution and its preparation method and application, in particular to a chiral polymer material containing L-amino acids (L-leucine, L-phenylglycine, L-phenylalanine ) group bonded chiral amino alcohol polymer polymer material, which belongs to the field of functional polymer materials. Background technique [0002] In recent years, chiral drugs have taken an increasing share of the drug market. The molecular structure of such drugs generally contains one or more chiral centers and exists in the form of enantiomers. Chirality plays an important role in everyday life, biochemistry and pharmaceutical industry. In living organisms, a pair of enantiomers often exhibit different pharmacological and toxicological properties. It is now generally accepted that sometimes the pharmacological effects of the two enantiomers are additive, but more often one enantiomer is active (active isomer) while ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/58C08F230/08C07C231/02C07C233/20
CPCC07C231/02C08F220/58C08F230/08C07C233/20
Inventor 刘丰良聂作兵刘锐利李翠钦冯思
Owner CENT SOUTH UNIV
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