Chiral sulfonamide derivative and preparation method and application thereof

A technology for sulfonamides and derivatives, applied in the field of chiral sulfonamide derivatives and their preparation, can solve the problems of unfavorable sulfonamide derivatives using industrial synthesis, non-recyclable chemical waste, low atom economy and the like , to achieve the effect of low cost, less waste and fewer reaction steps

Active Publication Date: 2019-01-04
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology solves problems associated with previous processes used by others that were complicated but effective at producing certain types of chemical products. It involves reacting an aminosulfonic acid derivative (an ester) on another molecule called benzene-1, which can be easier than existing techniques like making it from commercial sources. By doing this process we are able to produce various forms of these chemistry without requiring multiple reactions. These new ways make them more efficient compared to older methods while also being easy to use economically.

Problems solved by technology

This patented method for producing chirality Sulfarnes involves multiple step processes that require expensive equipment like inductive coupling techniques with specific types of reactants. These technical problem addressed in this patent include production costs associated with these procedures, complexity involved during manufacturing operations, environmental concerns related to waste products generated after each procedure, and potential safety hazards caused by residual unreacted starting materials used when preparing certain compounds.

Method used

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  • Chiral sulfonamide derivative and preparation method and application thereof
  • Chiral sulfonamide derivative and preparation method and application thereof
  • Chiral sulfonamide derivative and preparation method and application thereof

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[0088] The present invention synthesizes the preparation method of chiral sulfonamide derivatives, sulfonamide, imine, rhodium acetate, Molecular sieves are dissolved in an organic solvent to prepare a mixed solution; aryl diazoacetate is dissolved in an organic solvent to prepare a diazo compound solution; at -10°C, the diazo compound solution is added to the aforementioned mixed solution with a syringe pump; at the same time Stir vigorously; after the diazo compound solution is added dropwise, continue to stir for 60 minutes at -10°C until the diazo compound is completely consumed; the crude product is subjected to column chromatography (using ethyl acetate:petroleum ether=1:20~1: 10 is the eluent) to obtain pure product.

[0089] The synthesis reaction process is as follows:

[0090]

[0091] In reaction formula (II),

[0092] R is aryl or alkyl, selected from phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-methoxyphenyl, 3,4-dimethoxy phenyl, 2-thienyl, 2-...

Embodiment 1

[0097]

[0098] P-toluenesulfonamide (0.36mmol), p-chlorobenzylidene aniline (0.30mmol), rhodium acetate (0.006mmol), (R)-3,3'-bis(triphenylsilyl)binaphthol phosphate (0.03mmol), Molecular sieves (150 mg) were dissolved in 3.0 mL of anhydrous toluene to prepare mixed solution A; methyl phenyldiazoacetate was dissolved in 1.0 mL of anhydrous toluene to prepare diazo compound solution B; at -10 ° C, solution B At -10°C, the mixed solution A was added with a syringe pump within 1 hour. After injecting solution B, the reaction system was stirred at -10°C for 60 minutes. After the reaction was completed, the filtrate was filtered and the solvent was removed by rotary evaporation, and then the crude product was purified by column chromatography to obtain a pure product as a white solid. Its structure is shown in formula (a). The isolated yield of the product was 83%, the dr value was greater than 20:1, and the ee value was 99%. of the product 1 H NMR schematic as image 3 A...

Embodiment 2

[0101]

[0102] P-4-tert-butylbenzenesulfonamide (0.36mmol), p-chlorobenzylidene aniline (0.30mmol), rhodium acetate (0.006mmol), (R)-3,3'-bis(triphenylsilyl) Binaphthol phosphate (0.03mmol), Molecular sieves (150 mg) were dissolved in 3.0 mL of anhydrous toluene to prepare mixed solution A; methyl phenyldiazoacetate was dissolved in 1.0 mL of anhydrous toluene to prepare diazo compound solution B; at -10 ° C, solution B At -10°C, the mixed solution A was added with a syringe pump within 1 hour. After injecting solution B, the reaction system was stirred at -10°C for 60 minutes. After the reaction was completed, the filtrate was filtered and the solvent was removed by rotary evaporation, and then the crude product was purified by column chromatography to obtain a pure product as a white solid. Its structure is shown in formula (b). The isolated yield of the product was 78%, the dr value was greater than 20:1, and the ee value was 90%. of the product 1 H NMR schematic ...

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Abstract

The invention discloses a chiral sulfonamide derivative. The structural formula of the chiral sulfonamide ramification is shown in the description, wherein R is aryl, alkyl, cycloalkyl, heterocyclyl,substituted aryl, substituted alkyl and substituted heterocyclyl; Ar1 is aryl and substituted aryl; Ar2 is aryl, substituted aryl and heterocyclyl; Ar3 is aryl, substituted aryl and heterocyclyl; sulfonamide, aryl diazonium acetate and imine are taken as raw materials, 4-molecular sieve is taken as a water absorbing agent, rhodium acetate and chiral phosphoric acid are combined to be a catalytic system, and the chiral sulfonamide derivative is obtained by a one-step reaction in an organic solvent. The synthesis method has the advantages that the atomic economy is high, the selectivity is high,the yield is high, the reaction condition is mild, the operation is simple and safe; the chiral sulfonamide derivative with two quaternary carbon centers is a potential pharmaceutically active molecule, is widely used in the field of medicine, and has great application prospects.

Description

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Claims

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Application Information

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Owner SUN YAT SEN UNIV
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