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Trifluoromethanesulfonyl alkyne amide compound as well as preparation method and application thereof

A technology of trifluoromethanesulfonyl alkyne amides and amine compounds, which is applied in the field of hydrosulfhydration reaction of alkyne amides, can solve problems such as the instability of addition products, and achieve wide substrate applicability, fast reaction rate, and atom economy high effect

Active Publication Date: 2021-06-18
广州新肽生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although sulfhydryl modification reagents have been widely studied, they still face some challenges: such reagents need to have good selectivity, must be able to react in the aqueous phase, be able to complete the reaction efficiently, and the product needs to have good stability, etc.; For example, the addition product of maleimide is very unstable (Nat.Biotechnol.2012,30, 184–189)

Method used

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  • Trifluoromethanesulfonyl alkyne amide compound as well as preparation method and application thereof
  • Trifluoromethanesulfonyl alkyne amide compound as well as preparation method and application thereof
  • Trifluoromethanesulfonyl alkyne amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0088] Preparation of 1,1,1-trifluoromethyl-N-phenylethylsulfonamide:

[0089] Under ice-bath conditions, mix 5mmol phenethylamine and 10mmol triethylamine in dichloromethane solution and stir, slowly add 5mmol trifluoromethanesulfonyl chloride dropwise, add water after the reaction is complete, and extract the aqueous phase with dichloromethane Once, the organic phases were combined, washed once with saturated brine, the organic phase was separated, dried with anhydrous sodium sulfate, and the organic phase was concentrated to obtain 1,1,1-trifluoromethyl-N-phenylethylsulfonamide, light Yellow liquid, yield 92%. The following are the structural formula of the product and the experimental data of nuclear magnetic resonance and mass spectrometry:

[0090]

[0091] 1 HNMR (400MHz, CDCl 3 )δ7.33–7.13(m,5H),4.65(s,1H),3.02(s,2H),2.83(s,2H).

[0092] 13 C NMR (100MHz, CDCl 3 )δ139.4, 129.1, 128.1, 126.7, 121.1, 119.0, 116.8, 114.7, 46.4, 46.3, 463, 46.3, 35.6.

[0093] HR...

preparation Embodiment 2

[0095] Preparation of N-butyl-1,1,1-trifluoromethylsulfonamide:

[0096] Under ice-bath conditions, mix 5mmol n-butylamine and 10mmol triethylamine in dichloromethane solution and stir, slowly add 5mmol trifluoromethanesulfonyl chloride dropwise, add water after the reaction is complete, and extract the aqueous phase with dichloromethane Once, the organic phases were combined, washed once with saturated brine, the organic phase was separated, dried with anhydrous sodium sulfate, and the organic phase was concentrated to obtain N-butyl-1,1,1-trifluoromethylsulfonamide, light yellow Liquid, 92% yield. The following are the structural formula of the product and the experimental data of nuclear magnetic resonance and mass spectrometry:

[0097]

[0098] 1 H NMR (400MHz, CDCl 3 )δ4.47(s,1H),2.87(s,2H),1.51(s,2H),1.30(s,2H),0.90(s,3H).

[0099] 13 C NMR (100MHz, CDCl 3 )δ121.11, 118.97, 116.83, 114.68, 47.27, 47.24, 47.21, 47.18, 31.07, 20.45, 14.00.

[0100] HRMS(ESI)m / z ...

preparation Embodiment 3

[0102] Preparation of tert-butyl (2-((trifluoromethyl)sulfonyl)ethyl)carbamate:

[0103] Under ice-bath conditions, mix 5 mmol n-butyl (2-aminoethyl carbamate) and 10 mmol triethylamine in dichloromethane solution and stir, slowly add 5 mmol trifluoromethanesulfonyl chloride dropwise, and the reaction is complete After adding water, the aqueous phase was extracted twice with dichloromethane, the organic phases were combined, washed once with saturated brine, the organic phase was separated, dried with anhydrous sodium sulfate, and the organic phase was concentrated to obtain tert-butyl (2-((three Fluoromethyl)sulfonyl)ethyl)carbamate, light yellow liquid, yield 95%. The following are the structural formula of the product and the experimental data of nuclear magnetic resonance and mass spectrometry:

[0104]

[0105] 1 H NMR (400MHz, CDCl 3)δ8.52(s,1H),4.44(s,1H),3.42(s,2H),2.86(s,2H),1.42(s,9H).

[0106] 13 C NMR (100MHz, CDCl 3 )δ158.57, 121.11, 118.97, 116.83, 114.6...

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Abstract

The invention discloses a trifluoromethanesulfonyl alkyne amide compound as well as a preparation method and application thereof. Based on hydrosulfide reaction of the alkyne amide and sulfydryl, selective modification and marking of sulfydryl in polypeptide and protein are realized. The compound has good stability. Reaction with sulfydryl only can be selected, and other active groups on the polypeptide or protein are not affected; the method has the advantages of high reaction rate, no side reaction, simple and mild reaction conditions, easiness in operation, wide substrate applicability, high atom economy and the like. The compound has good stability under acid-base and oxidation conditions, can stably exist for several months at normal temperature, and provides a new steady way for selective modification and marking of sulfydryl in biological coupling, polypeptide and / or protein.

Description

technical field [0001] The present invention relates to the hydrogen sulfhydration reaction of alkyne amides, in particular to a trifluoromethanesulfonyl alkyne amides compound and its preparation method and the use of the compound in hydrogen sulfhydration reaction, and the use of the compound in polypeptide and / or protein Sulfhydryl groups are selectively modified and labeled. The invention belongs to the technical field of organic chemical synthesis and chemical modification of polypeptide and / or protein. Background technique [0002] Proteins are biological macromolecules with important biological activities formed by connecting natural α-amino acids in a certain order through amide bonds. They are the material basis of life and play an extremely important role in life activities. Proteins often need to be modified when they perform their functions. At the same time, people also need to modify and label proteins in order to study the biological functions and activities ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/09C07D311/12C07C303/38C07K5/062C07K5/037C07K7/06C07K7/16C07K1/107C07K1/13
CPCC07C311/09C07D311/12C07K5/06026C07K5/0215C07K7/06C07K7/16C07K1/1077C07K1/13C07C2601/14
Inventor 赵军锋王长流
Owner 广州新肽生物医药科技有限公司
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