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Chiral vicinal diamine compound and method for preparing same

A technology for ortho-diamine compounds, applied in the field of chiral ortho-diamine compounds and their preparation, to achieve the effects of simple reaction raw materials, rich product structure types, and easy-to-obtain reaction raw materials

Active Publication Date: 2016-07-13
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of system is currently limited to N-aryl or alkyl-protected meso-aziridines, and the organic amines used can only be aromatic primary amines

Method used

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  • Chiral vicinal diamine compound and method for preparing same
  • Chiral vicinal diamine compound and method for preparing same
  • Chiral vicinal diamine compound and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Under an argon atmosphere, silver hexafluoroantimonate (0.0025 mmol), (S)-DTBM-SEGPHOS (0.00375 mmol) and dry m-xylene (0.25 mL) were successively added to a dry Schlenk tube, and stirred at room temperature for 30 minutes 2-Phenyl-N-p-toluenesulfonyl aziridine (0.22mmol) and aniline (0.1mmol dissolved in 0.25mL dry m-xylene) were added in sequence, and the reaction was stirred at 15°C for 10 hours (monitored by TLC). After completion of the reaction, add saturated aqueous sodium bicarbonate solution (5mL) to stop the reaction, extract with ethyl acetate (5mL×3), dry over anhydrous magnesium sulfate, and remove the solvent under reduced pressure to obtain the crude product. The mixed solvent of 1 (containing 0.5v% triethylamine) is used as a developing agent, and the product is separated by 300-400 mesh silica gel column chromatography, and its enantiomeric ratio (e.r. value) is determined by the HPLC method of a chiral stationary phase, and the yield : 35.5 mg, yield: ...

Embodiment 2

[0033]Under an argon atmosphere, silver hexafluoroantimonate (0.0025 mmol), (S)-DTBM-SEGPHOS (0.00375 mmol) and dry m-xylene (0.25 mL) were successively added to a dry Schlenk tube, and stirred at room temperature for 30 minutes Add 2-phenyl-N-p-toluenesulfonyl aziridine (0.22mmol) and 4-methoxyaniline (0.1mmol dissolved in 0.25mL dry m-xylene) in sequence, and then stir the reaction at 15°C for 10 hours (TLC monitoring). After the reaction was completed, saturated aqueous sodium bicarbonate solution (5 mL) was added to terminate the reaction, extracted with ethyl acetate (5 mL×3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The mixed solvent of 1 (containing 0.5v% triethylamine) is used as a developing agent, and the product is separated by 300-400 mesh silica gel column chromatography, and its enantiomeric ratio (e.r. value) is determined by the HPLC method of a chiral stationary phase, and the yield ...

Embodiment 3

[0037] The operation of reaction is with embodiment 2, but solvent used is different, and concrete operation is as follows:

[0038] Under an argon atmosphere, silver hexafluoroantimonate (0.0025 mmol), (S)-DTBM-SEGPHOS (0.00375 mmol) and dry dichloromethane (0.25 mL) were successively added to a dry Schlenk tube, and stirred at room temperature for 30 minutes Add 2-phenyl-N-p-toluenesulfonyl aziridine (0.22mmol) and 4-methoxyaniline (0.1mmol dissolved in 0.25mL dry dichloromethane) in sequence, and then stir the reaction at 15°C for 12 hours (TLC monitoring). After the reaction was completed, saturated aqueous sodium bicarbonate solution (5 mL) was added to terminate the reaction, extracted with ethyl acetate (5 mL×3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The mixed solvent of 1 (containing 0.5v% triethylamine) is used as a developing agent, and the product is separated by 300-400 mesh silica gel...

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Abstract

The invention discloses a chiral vicinal diamine compound and a method for preparing the same.The method includes catalyzing organic amine and substituted racemic or meso N-sulfonyl ethylene imine under by the aid of a catalyst system with univalent silver salt and chiral diphosphine ligands at the temperatures of 15-40 DEG C to carry out asymmetric ring-opening reaction so as to synthesize the chiral vicinal diamine compound.The chiral vicinal diamine compound and the method have the advantages that the chiral vicinal diamine compound can be prepared in a catalytic asymmetric ring-opening mode, the method is applicable to the racemic or meso N-Ts ethylene imine, reaction raw materials are simple and are easily available, reaction conditions are mild, products are abundant in structure types, and the chiral vicinal diamine and the method are high in yield and stereoscopic selectivity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and specifically relates to a chiral ortho-diamine compound and a preparation method thereof. Background technique [0002] Chiral ortho-diamine compounds are a class of molecules that play a very important role in the research fields of organic synthesis and medicinal chemistry. On the one hand, they exist as core skeletons in many important biological activities and medicinal values: for example, the drug Oseltamvir (Chinese trade name: Tamiflu) for the treatment of influenza A and B; Nutlin-3 is a A highly efficient and selective Mdm2 antagonist with an IC50 of 90nM in a cell-free assay, in which optically pure (-)-Nutlin-3 has a higher activity. It is widely used as a small molecule probe in chemical biology and is used for cancer In the study of chemotherapy treatment (Nature, 2004, 432, 307; Science, 2004, 303, 844). On the other hand, chiral ortho-diamin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/21C07D215/06C07D209/08C07D295/135C07C303/40
CPCC07B2200/07C07C303/40C07C311/21C07D209/08C07D215/06C07D295/135
Inventor 柴卓杨培俊王绍武杨高升
Owner ANHUI NORMAL UNIV
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