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Chiral diamine intermediate and preparation method and application thereof

A technology for chiral diamines and intermediates, which is applied in the field of chiral diamine intermediates and their preparation, can solve the problems of synthesis and application limitations of azamacrocyclic compounds, and achieve simple and controllable reaction temperature and low raw material price. Inexpensive and easy to obtain, low by-product effect

Inactive Publication Date: 2018-03-27
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such intermediates of amino acid compounds are rare at home and abroad, and their application in the synthesis of azamacrocyclic compounds is even rarer. Only a few cases have been seen abroad, and there are basically no such intermediates in China.
This has greatly restricted the synthesis and application of azamacrocyclic compounds.

Method used

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  • Chiral diamine intermediate and preparation method and application thereof
  • Chiral diamine intermediate and preparation method and application thereof
  • Chiral diamine intermediate and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] In a 250ml round bottom flask, m-phenylenediamine (1.08g, 0.01mol) was added, and then a small amount of dichloromethane was added and stirred to dissolve, while the temperature was set at 50°C. After m-phenylenediamine was completely dissolved, N-Boc phenylalanine (5.30 g, 0.02 mol) was added, followed by condensation agent DCC (4.12 g, 0.02 mol), and DMAP catalyst (0.61 g, 0.005 mol). After all the raw materials have been added, dichloromethane is added to make the total volume 180ml. After reacting for 6 hours, spin the reacted solution to dryness, mix the sample with silica gel, put it on the column by dry method, and use thin-layer chromatography to spot the plate twice until the R of the intermediate product point is determined. f value, and then subjected to column separation, the eluent was methanol / dichloromethane (the volume ratio of methanol / dichloromethane was 0:100-50:50), and an intermediate product was obtained. After weighing the obtained intermediate p...

Embodiment 2

[0041] In a similar manner to Example 1, the relative addition ratios of m-phenylenediamine, N-Boc phenylalanine, and DMAP catalysts were changed.

[0042] In a 250ml round bottom flask, m-phenylenediamine (1.08g, 0.01mol) was added, and then a small amount of dichloromethane was added and stirred to dissolve, while the temperature was set at 50°C. After m-phenylenediamine was completely dissolved, N-Boc phenylalanine (7.96 g, 0.03 mol) was added, followed by condensation agent DCC (4.12 g, 0.02 mol), and DMAP catalyst (1.22 g, 0.01 mol). After all the raw materials were added, dichloromethane was added to make the total volume 180ml. After reacting for 6 hours, spin the reacted solution to dryness, mix the sample with silica gel, put it on the column by dry method, and use thin-layer chromatography to spot the plate twice until the R of the intermediate product point is determined. f Value, and then column separation, the eluent is methanol / dichloromethane (the volume ratio ...

Embodiment 3

[0044] According to the similar method of embodiment 1, prolong the reaction time that the first step connects amino acid. In a 250ml round bottom flask, m-phenylenediamine (1.08g, 0.01mol) was added, and then a small amount of dichloromethane was added and stirred to dissolve, while the temperature was set at 50°C. After m-phenylenediamine was completely dissolved, N-Boc phenylalanine (5.30 g, 0.02 mol) was added, followed by condensation agent DCC (4.12 g, 0.02 mol), and DMAP catalyst (0.61 g, 0.005 mol). After all the raw materials were added, dichloromethane was added to make the total volume 180ml. After reacting for 10 hours, spin the reacted solution to dryness, mix the sample with silica gel, put it on the column by dry method, and use thin-layer chromatography to spot the plate twice until the R of the intermediate product point is determined. f Value, and then column separation, the eluent is methanol / dichloromethane (the volume ratio of methanol / dichloromethane is ...

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Abstract

The invention belongs to the technical field of organic chemistry and discloses a chiral diamine intermediate and a preparation method and application thereof. The structural formula of the chiral diamine intermediate is shown in the formula 1, The preparation method utilizes a three-step preparation technology and comprises that 1, m-phenylenediamine as a reaction raw material is grafted with phenylalanine at 10-50 DEG C in a dichloromethane solvent in the presence of a DCC condensing agent and a DMAP catalyst in 3-48h, 2, through silica gel column chromatography, an intermediate product witha protection group is separated, and 3, the protection group is removed through an acid (according to a strong acid use amount of 0.4-2ml in each unit weight of the intermediate product) in 30min-24hso that a crude product is obtained. The compound has a unique chiral center, can produce a special hydrogen bonding function and can be used as an excellent chiral amine intermediate for researchingazamacrocycles. The azamacrocycles prepared from the compound can contain small molecules and ions and lay the foundation for chiral recognition.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a chiral diamine intermediate and a preparation method and application thereof. Background technique [0002] Chirality is a basic feature ubiquitous in nature. Not only is chirality widespread in the macroscopic world, such as human hands and conch shells that rotate in different directions, but also many microscopic material molecules have three-dimensional forms that are similar to mirror images and cannot be superimposed. In organisms, the existence of a single enantiomer is a common phenomenon, such as: the amino acids that make up proteins are all L-amino acids, while the monosaccharides that make up polysaccharides and ribose are D-monosaccharides, and the chiral structure (such as Enzyme-catalyzed asymmetric synthesis, chiral replication) and chiral phenomena (such as chiral recognition, single-helix morphology) are almost ubiquitous in living syste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C237/20
CPCY02P20/55C07C237/20C07C231/12C07C269/06C07C271/22
Inventor 曹芳利成晓玲周浩温炳松李文奎
Owner GUANGDONG UNIV OF TECH
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