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Double-substituted 6-alkyl imidazolium-6-ammonium-beta-cyclodextrin with double positive electricity centers and preparation method thereof

A technology of cyclodextrin and alkylimidium, which is applied in the field of chiral separation of racemates, can solve the problems of weak resolution ability of mandelic acid drugs and limited resolution ability of amino acid compounds, etc., and achieve excellent resolution ability , good water solubility, efficient split effect

Active Publication Date: 2013-08-07
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the positively charged CDs are ammonium or imidazolium-based single positive center-β-cyclodextrin, and the ammonium positively charged CD has excellent resolution ability for mandelic acid drugs, but the resolution of amino acid compounds The ability is very limited; while the imidazolium-based positively charged CD has good resolution ability for amino acid compounds, but the resolution ability for mandelic acid drugs is weak (① W.H. Tang, S.C. Ng, Monosubstituted positively charged cyclodextrins: Synthesis and applications in chiral separation, J. Sep. Sci. 2008, 31, 3246 – 3256;② V. Cucinotta, A. Contino, A. Giuffrida, G. Maccarrone, M. Messina, Application of charged single isomer derivatives of cyclodextrins in capillary electrophoresis for chiral analysis, J. Chromatogr. A 2010, 1217, 953-967.)

Method used

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  • Double-substituted 6-alkyl imidazolium-6-ammonium-beta-cyclodextrin with double positive electricity centers and preparation method thereof
  • Double-substituted 6-alkyl imidazolium-6-ammonium-beta-cyclodextrin with double positive electricity centers and preparation method thereof
  • Double-substituted 6-alkyl imidazolium-6-ammonium-beta-cyclodextrin with double positive electricity centers and preparation method thereof

Examples

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preparation example Construction

[0022] In conjunction with the accompanying drawings, the preparation method of the 6-alkylimidazolium-6-ammonium-β-cyclodextrin of the double-substituted double positive center of the present invention comprises the following steps:

[0023] In the first step, based on the mechanism of nucleophilic substitution, p-toluenesulfonyl chloride and imidazole often undergo a warm reaction in dichloromethane to obtain p-toluenesulfonyl imidazole;

[0024] In the second step, the product p-toluenesulfonylimidazole obtained in the first step is placed in an aqueous solution in which β-cyclodextrin is dissolved, stirred and reacted at room temperature for 2 to 4 hours, then 10 to 30% aqueous sodium hydroxide solution is added, and the resulting A small amount of precipitate; Utilize the low solubility of the generated Ts-CD at neutral or near-neutral, add ammonium chloride to the filtrate to adjust its pH value to 6~8 to obtain a white solid substance, filter to obtain the product p-tolu...

Embodiment 1

[0038] Implementation example 1: The preparation method of the present invention's double-substituted double positive center 6-ammonium-6-methylimidazolium-β-cyclodextrin chiral resolving agent comprises the following steps:

[0039] In the first step, take a 250 mL double-necked round-bottom flask and vacuumize it first, then blow it with nitrogen, weigh p-toluenesulfonyl chloride (6.57 g, 34.5 mmol) into the flask, then add 30 mL of dry dichloromethane, and stir to dissolve , then weigh imidazole (5.3 g, 77.8 mmol) and dissolve in 30 mL of dry dichloromethane solution, transfer to the dropping funnel, drop the above solution into the flask (1~2 drops / second), stir at room temperature overnight. After the reaction was completed and filtered, the filtrate was concentrated to ~10 mL and dropped into 40 mL of n-hexane solution, a white solid was precipitated, filtered under reduced pressure, the precipitate was washed with n-hexane, and vacuum-dried to obtain the product p-tolue...

Embodiment 2

[0050] Implementation Example 2: The preparation method of the present invention's double-substituted double positive center 6-ammonium-6-ethylimidazolium-β-cyclodextrin chiral resolving agent comprises the following steps:

[0051] The first step is the same as the first step in Example 1;

[0052] The second step is the same as the second step of Example 1;

[0053] The third step is the same as the third step of example 1;

[0054] The fourth step is the same as the fourth step of Example 1

[0055] The fifth step is to prepare ethylimidazole first: take a 50 mL two-necked flask, vacuum it first and then pass nitrogen, weigh imidazole (4 g, 58.8 mmol) into the flask, then measure 20 mL of dry ethanol into the flask, and stir for a while . Then sodium ethoxide (4.4 g, 64.6 mmol) was added into the flask, the temperature was raised to 40° C., and the mixture was stirred for half an hour. Measure bromoethane (7.04 g, 64.6 mmol) into the dropping funnel, drop it into the fl...

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Abstract

The invention discloses double-substituted 6-alkyl imidazolium-6-ammonium-beta-cyclodextrin with double positive electricity centers and a preparation method thereof. The structural formula of double-substituted 6-imidazolidinylnio-6-ammonium-beta-cyclodextrin is as shown in the specification. The preparation method comprises the following steps: adding imidazole in 4-methyl-benzene sulfonyl chloride and then reacting with beta-cyclodextrin so as to obtain 6-p-methyl-benzene-sulfonyl-beta-cyclodextrin (Ts-CD) the 6-hydroxyl of which is substituted; reacting Ts-CD with sodium azide so as to obtain 6-azido-beta-cyclodextrin, namely, N3-CD; reacting N3-CD with 2,4,6-trimethyl benzene sulfonyl chloride so as to obtain 6-azido-6-(2,4,6-trimethyl benzene sulfonyl)-beta-cyclodextrin, namely, N3-Mess-CD; reacting N3-Mess-CD with alkyl imidazole so as to obtain double-substituted 6-azido-6-alkyl imidazolium-beta-cyclodextrin, and reducing azido to amino with triphenylphosphine so as to obtain double-substituted 6-amino-6-alkyl imidazolium-beta-cyclodextrin; and carrying out amino hydrochlorination and ion exchange so as to obtain double-substituted 6-alkyl imidazolium-6-ammonium-beta-cyclodextrin with the double positive electricity centers. The obtained cyclodextrin has good water solubility and effective chiral resolution capacity.

Description

technical field [0001] The invention belongs to the field of chiral resolution of racemates, in particular to a class of 6-ammonium-6-alkylimidazoliums with double-substituted double positive centers used in capillary electrophoresis to achieve chiral resolution of racemates base-β-cyclodextrin. Background technique [0002] β-Cyclodextrin (β-Cyclodextrin, β-CD) is a circular oligosaccharide molecule in the shape of a truncated cone, which is connected by 7 D-glucose molecules by α-(1,4) glycosidic bonds. The inside of the cavity is shielded by two rings of hydrogen atoms (H-3 and H-5) and a ring of glycosidic bonded oxygen atoms under the shield of the C-H bond, so the inner cavity of the cyclodextrin is hydrophobic, and the cyclodextrin molecule The outer frame is hydrophilic due to the aggregation of hydroxyl groups. The cavity-like hydrophobic cavity based on cyclodextrin, under the influence of steric effect, becomes a supramolecular system with molecular recognition ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16C07B57/00
Inventor 唐卫华戴云唐键王树叶吴剑骅杨三东
Owner NANJING UNIV OF SCI & TECH
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