Preparation method of trifluoromethylated polypeptide compounds

A technology of trifluoromethylation and peptide compounds, applied in the fields of peptides and organic chemistry, which can solve the problems of reducing functional group compatibility and atom economy

Active Publication Date: 2022-03-18
杭州肽佳生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduction and subsequent removal of protecting groups not only requires additional manipulations, such as removal of protecting groups (Piv, Ac, Boc, etc.) Important functional groups are sensitive to acids and bases, moreover, introduction of direct groups reduces atom economy

Method used

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  • Preparation method of trifluoromethylated polypeptide compounds
  • Preparation method of trifluoromethylated polypeptide compounds
  • Preparation method of trifluoromethylated polypeptide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add 3ml of a mixed solvent of DMF and water to 127.2mg (0.4mmol) of Boc-Trp-OMe (purchased from Shanghai Beide Pharmaceutical Technology Co., Ltd., article number: BD118484-10g, batch: ALZ812, bottle number: N16-418) (The volume ratio of DMF to water is 1:4), add 252mg (0.8mmol) 1-(trifluoromethyl)-1,2-phenyliodide-3(1H)-one, 5.3mg (0.016 mmol) fluorescein, react for 3 hours under the irradiation of 9w blue LED light at room temperature, after the reaction, carry out the extraction operation: 1. Add saturated NaCl aqueous solution and ethyl acetate to the reaction solution for extraction twice, 2. Add for the first time Saturated NaCl aqueous solution 40mL, ethyl acetate 30mL, conduct one extraction, 3. After the first extraction is completed, collect the organic layer, take the water phase layer and add 20ml ethyl acetate for the second extraction, after the extraction is completed, take the organic layer and pass through anhydrous sulfuric acid Sodium-drie...

Embodiment 2

[0036] Except that the mass and moles of 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H)-one were changed to 126.4 mg (0.4 mmol), and the mass and moles of fluorescein were changed to 1.328 mg (0.004mmol), other operation is constant, and operating procedure is with embodiment 1, obtains compound pure product 46.32mg shown in formula 2a, and reaction yield is 30%.

Embodiment 3

[0038] In addition to changing the mass and moles of 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H)-one to 379.2 mg (1.2 mmol), the mass and moles of fluorescein to 66.4 mg (0.2mmol), other operation is constant, and operating procedure is with embodiment 1, obtains the compound pure product 58.67mg shown in formula 2a, and reaction yield is 38%.

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Abstract

The invention discloses a method for preparing a trifluoromethylated polypeptide compound represented by formula (II), the method comprising the following steps: using a mixed solvent of DMF and water with a volume ratio of 1:1-4 As the reaction medium, the polypeptide compound as shown in formula (I) and 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H)-ketone react 3-3 at room temperature under blue light in photocatalyst After 8 hours, after the reaction is complete, the resulting reaction mixture is post-treated to obtain trifluoromethylated polypeptide compounds represented by formula (II). The present invention drives the reaction under visible light irradiation, and the reaction solvent is a mixed solvent of DMF and water, which is more in line with the concept of green chemistry, green, and environmentally friendly. The product can be prepared in one step, the operation process is simple, and the source of raw materials has been commercialized and easily obtained. Using photocatalyst, it has good catalytic performance, mild reaction conditions and high site selectivity.

Description

(1) Technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for preparing trifluoromethylated polypeptide compounds, in particular to a new method for preparing trifluoromethylated polypeptide compounds by direct trifluoromethylation of polypeptide compounds . (2) Background technology [0002] Peptide is a compound formed by α-amino acids linked together by peptide bonds, and it is also an intermediate product of protein hydrolysis. Many active substances in the human body exist in the form of peptides. Peptides are involved in various fields of human hormones, nerves, cell growth and reproduction. Its importance lies in regulating the physiological functions of various systems and cells in the body, activating relevant enzyme systems in the body, promoting the permeability of intermediate metabolic membranes, or controlling DNA transcription or Affect specific protein synthesis, and finally produce s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/20C07K5/078C07K5/065C07K5/062
CPCC07D209/20C07K5/06139C07K5/06017C07K5/06026C07K5/06078
Inventor 朱勍张方方
Owner 杭州肽佳生物科技有限公司
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