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Chirality amine containing imidazole sulfur ether structure and preparation method and usage thereof

A technology of chiral amine and azole sulfide, applied in the application of chiral amine in asymmetric catalytic synthesis, the field of preparation of chiral amine, to achieve the effect of good chiral induction properties

Active Publication Date: 2007-09-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Combining amino acids with thioethers to synthesize a new class of chiral amines containing imidazole thioether structures and their protonic acid salt catalysts has not been reported at home and abroad

Method used

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  • Chirality amine containing imidazole sulfur ether structure and preparation method and usage thereof
  • Chirality amine containing imidazole sulfur ether structure and preparation method and usage thereof
  • Chirality amine containing imidazole sulfur ether structure and preparation method and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Preparation of 2-((S)-2-aminopropylthio)-1-hexylimidazole

[0041] Add (S)-1-(bromomethyl)ethylamine hydrobromide (21.90g, 0.1mol), 2-mercapto-1-hexylimidazole (18.41g, 98%, 0.1mol) and ethanol in a 100mL three-necked flask (60mL), reflux reaction for 12h, after neutralization, desolvation under reduced pressure, washed with ethyl acetate (2 × 20mL), after distillation to remove the solvent, column chromatography separation and purification to obtain the target compound (22.85g, yield 95% ), its specific rotation [α] D 20 =+32.1°.

Embodiment 2

[0042] Example 2: Preparation of 2-((S)-2-aminopropylthio)-1-methylimidazole

[0043] (S)-1-(bromomethyl)ethylamine hydrobromide (21.90g, 0.1mol), 2-mercapto-1-methylimidazole (18.41g, 98%, 0.1mol) and 1,2-dichloroethane (60mL), reflux reaction for 12h, after neutralization, desolvation under reduced pressure, washed with ethyl acetate (2 × 20mL), and then distilled to remove the solvent to obtain the target compound (16.20g, yield 95%), its specific rotation [α] D 20 =+33.2°.

Embodiment 3

[0044] Example 3: Preparation of 2-((S)-2-aminobutylthio)-1-ethylimidazole

[0045] Add (S)-1-(chloromethyl)propylamine hydrochloride (14.4g, 0.1mol), 2-mercapto-1-ethylimidazole (12.82g, 98%, 0.1mol) and acetonitrile ( 10mL), reflux reaction for 12h, after neutralization, desolventization under reduced pressure, washing with ethyl acetate (2 × 20mL), and distillation to remove the solvent, separation and purification by column chromatography to obtain the target compound (14.95g, yield 75%) , its specific rotation [α] D 20 =+33.5°.

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Abstract

The invention discloses a making method chiral amine protonic acid salt with general formula as I and II, which comprises the following steps: dissolving halogenated aliphatic amine haloid acid salt of chiral amino acid derivant as formula III or IV and mercapto imidazole substituted by N-R3 as formula V into organic solvent to do substituted reaction; neutralizing the reacting liquid; obtaining the product as chiral agent, catalyst and chiral material.

Description

(1) Technical field [0001] The invention relates to a chiral amine containing an imidazole sulfide structure, which belongs to new chemical materials. The invention also relates to a preparation method of the chiral amine containing an imidazole sulfide structure and the chiral amine containing an imidazole sulfide structure Applications in asymmetric catalytic synthesis. (2) Background technology [0002] Asymmetric catalysis is one of the most active fields of chemical development today, and it is a strong theoretical basis and academic basis for the development of chiral drugs, materials, spices and other chemicals. Enzymes and metal complexes are the two most important and effective catalysts, among which metal complexes are the most common chemical catalysts studied, and have achieved world-renowned achievements, some of which have been applied to industrial production. The Nobel Prize in 2001 The Bell Prize in Chemistry is awarded to three scientists who have made out...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/84C07D403/12B01J31/02
Inventor 许丹倩罗书平岳华栋王益锋徐振元
Owner ZHEJIANG UNIV OF TECH
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