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Chiral quaternary phosphonium salt phase transfer catalyst, preparation method and application thereof

A technology of phase transfer catalysts and quaternary phosphonium salts, which is applied in organic chemical methods, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of few catalytic examples, achieve stable air and water performance, diverse structures, and easy The effect of the operation

Active Publication Date: 2019-05-07
四川六泰科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the reported quaternary phosphonium salts are monofunctional rigid catalysts, and there are few examples of bifunctional chiral phosphonium salts with flexible skeletons.

Method used

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  • Chiral quaternary phosphonium salt phase transfer catalyst, preparation method and application thereof
  • Chiral quaternary phosphonium salt phase transfer catalyst, preparation method and application thereof
  • Chiral quaternary phosphonium salt phase transfer catalyst, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (S)-Methyl(3-methyl-2-(4-methylbenzenesulfonamide)butyl)diphenyl iodide , the structural formula is:

[0050]

[0051] Concrete preparation process is as follows:

[0052] (1) Reflux reaction of valine with hydrochloric acid / methanol solution for 5 hours, spin the solvent, then add TsCl and triethylamine, react at room temperature for 3 hours, and obtain compound 2 through extraction and concentration; wherein, valine, TsCl and triethylamine The molar ratio of ethylamine is 1:1.2:2;

[0053] (2) Dissolve compound 2 in an organic solvent, then add LiAlH 4 React at room temperature for 3 h, filter, and react the filtered product with EsCl and triethylamine for 3 h to obtain compound 3; wherein, compound 2, LiAlH 4 , the mol ratio of EsCl and triethylamine is 1:2:1.2:2;

[0054] (3) Compound 3 was added to NaOH aqueous solution, stirred at room temperature for 3 h, extracted and concentrated to obtain Compound 4;

[0055] (4) Compound 4 and KPPh 2 Mix according to t...

Embodiment 2

[0061] ((S)-2-(S)-2-((tert-butoxycarbonyl)amino)-3-methylbutylamine)-3-methylbutyl(methyl)(methyl) Diphenylammonium iodide , the structural formula is:

[0062]

[0063] The specific preparation process is as follows: according to the preparation method of Example 1, its starting material is also valine, and the replacement group is replaced according to the above structure in the reaction process, and finally tert-butyl-1-(((s) -1-(diphenylphosphine)-3-methylbutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate,

[0064] Add tert-butyl-1-(((s)-1-(diphenylphosphine)-3-methylbutan-2-yl)amino)-3-methyl-1-oxobutane to the reaction flask -2-yl) carbamate 470mg (1.0mmol), iodomethane 170mg (1.2mmol) and 20ml tetrahydrofuran, reacted at room temperature for 2h, and concentrated to obtain 575.3mg of the product with a yield of 94%.

[0065] NMR and MS data: 1 H NMR (400MHz, CD 3 OD)δ8.00-7.79(m,6H),7.77-7.67(m,4H),4.21-4.05(m,1H),3.63(d,J=6.2Hz,1H),3.50-3.35(m,1H ), 3.24(td...

Embodiment 3

[0067] ((S)-2-((R)-2-((tert-butoxycarbonyl)amino)-3-methylbutylamine)-3-methylbutyl(methyl)(methyl) Diphenylammonium iodide , the structural formula is:

[0068]

[0069] Concrete preparation process is as follows:

[0070] According to the preparation method of Example 1, the starting material is also valine, and the replacement group is replaced according to the above structure in the reaction process, and finally tert-butyl-1-(((s)-1-(di Phenylphosphine)-3-methylbutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate, add tert-butyl-1- (((s)-1-(diphenylphosphine)-3-methylbutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)carbamate 470mg( 1.0 mmol), 170 mg (1.2 mmol) of methyl iodide and 20 ml of tetrahydrofuran, reacted at room temperature for 5 h, and concentrated to obtain 599.3 mg of the product, with a yield of 98%.

[0071] NMR and MS data: 1 H NMR (400MHz, CD 3 OD)δ7.94-7.77(m,6H),7.75-7.65(m,4H),4.20-4.04(m,1H),3.74(d,J=5.8Hz,1H),3.37-3.19(m,2H ), 2.72(d, J=14.0Hz, ...

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Abstract

The invention provides a chiral quaternary phosphonium salt phase transfer catalyst, a preparation method and application thereof. The catalyst is prepared from natural amino acid as the starting rawmaterial, has wide raw material sources, and is simple in synthesis. The catalyst has a plurality of modification sites, structural diversity and strong controllability, also has multiple hydrogen bond donor sites, has strong chiral induction catalytic ability, at the same time has stability to air and water, is easy to store, has good water solubility, is environment-friendly, and has strong practicability and industrial application value.

Description

technical field [0001] The invention belongs to the technical field of phase transfer catalysts, in particular to a chiral quaternary phosphonium salt phase transfer catalyst and its preparation method and application. Background technique [0002] In recent years, the application of chiral phase transfer catalysts in organic chemistry has been rapidly developed. Phase transfer catalysts can make heterogeneous reactions proceed under mild conditions, speed up the reaction rate, and significantly increase the yield. This technology has been widely used in laboratories and industries. As a type of phase transfer catalyst, quaternary phosphonium salts have the advantages of high thermal stability, good catalytic efficiency, recyclability and low toxicity. As phase transfer catalysts, they are widely used in the synthesis of various important bioactive molecules and drug molecules. Chiral quaternary phosphonium salts are mainly divided into two types: carbon phosphonium type (M...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07B53/00C07D307/80C07D513/10C07D513/20C07F9/54
Inventor 王天利徐志鹏
Owner 四川六泰科技有限公司
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