Synthesis method of alpha, alpha-difluoro-gamma-hydroxyacetamide derivative

A technology of glycolamide and bromodifluoroacetanilide, which is applied in the field of synthesis of α,α-difluoro-γ-hydroxyacetamide derivatives, can solve the problem of single substrate and achieve good substrate applicability and reaction The effect of good selectivity and good application prospects
CN112574056AActive Publication Date: 2021-03-30ZHEJIANG UNIV OF TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG UNIV OF TECH
Publication Date
2021-03-30

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Abstract

The invention discloses a synthesis method of an alpha, alpha difluoro gamma hydroxyacetamide derivative, which comprises the following steps: dissolving a bromo difluoro acetanilide compound shown ina formula (II), a photocatalyst and an organic alkali in an olefin derivative shown in a formula (I), reacting at room temperature for 5-24 hours under the irradiation of visible light, and after thereaction is finished, filtering to obtain the alpha, alpha difluoro gamma hydroxyacetamide derivative. A reaction system is subjected to post-treatment to obtain the alpha, alpha difluoro gamma hydroxyacetamide derivative shown in the formula (III), and the reaction formula is shown in the specification, in the formula (I) and the formula (III), a substituent group R1 is C2-C11 linear alkyl, arylor substituted aryl; in the formula (II) and the formula (III), the substituent R2 is H, methyl, methoxy, fluorine, chlorine, bromine or aromatic heterocycle. According to the invention, light is used as a reaction energy source to realize hydroxylation of olefin acetamide, so that the reaction is safer and greener, the cost is lower, the substrate application range of the reaction is expanded, and a simpler and more convenient method for preparing the alpha, alpha-difluoro gamma-hydroxyacetamide compound is provided.
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Description

technical field

[0001] The invention relates to a synthesis method of α,α-difluoro-γ-hydroxyacetamide derivatives. Background technique

[0002] The introduction of fluorine atoms into the drug structure will change the lipophilicity, metabolic stability, bioavailability and other properties of the compound, which is a common method for new drug design. Difluoroalkyl alcohol compounds have been widely used in the synthesis of active molecules such as nucleotide analogs and enzyme inhibitors (for example: (a) Xu, Y.; Prestwich, G.D.Org.Lett.2002,4,4021. (b) Matulic-Adamic J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (c) Ladame, S.; Willson, M.; .Org.Chem.2002, 2640.(d) Butt, A.H.; Percy, J.M.; Spencer, N.S.Chem.Commun.2000, 1691.(e) Lopin, C.; , S.R.J. Am. Chem. Soc. 2002, 124, 14668.). In addition, studies have shown that difluoroketones have weak nucleophilicity, and medicinal chemists have used this property to design a series of protease inhibitors, which ...

Claims

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