Method for synthesizing high-selectivity oxaziridine through chemical enzyme process

An oxaziridine and high-selectivity technology is applied in the field of chemical-enzymatic synthesis of high-selectivity oxaziridine, and can solve the problems of harmful environment and cumbersome production process.

Active Publication Date: 2018-02-27
JILIN UNIV
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Problems solved by technology

The traditional synthetic method of oxaziridine is chemical method, and traditional chemical method often uses the mode of catalytic imine oxide such as m-chloroperoxybenzoic acid, acetic anhydride, transition state metal to prepare oxaziridine (L.Martiny and K.A. J.Chem.Soc., Perkin Trans.1,1995,699.), the reagents used are harmful to the environment and the production process is cumbersome and has by-products

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  • Method for synthesizing high-selectivity oxaziridine through chemical enzyme process
  • Method for synthesizing high-selectivity oxaziridine through chemical enzyme process
  • Method for synthesizing high-selectivity oxaziridine through chemical enzyme process

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Embodiment 1

[0023] 1. Experimental instruments and reagents

[0024] The experimental raw materials and instruments used in the embodiments of the present invention are shown in Table 1.

[0025] Table 1 Experimental Instruments and Reagents

[0026]

[0027]

[0028] a : Candida Antarctica lipase B (CALB, 10000U / mL) b : Novozyme 435 (the commercial immobilized CALB, 15000U / g)

[0029] 2. Determination of the best reaction conditions

[0030] The oxidation reaction between benzaldehyde and n-butylamine was chosen as a model, and benzaldehyde, n-butylamine, lipase, oxidant, peroxyacid precursor and solvent were mixed in a round bottom flask, and the reaction was stirred at room temperature. Detect the reaction process with TLC, after the reaction finishes, the reaction mixture is extracted twice with ethyl acetate, and the organic layer is washed with anhydrous Na 2 SO 4 Dry and concentrate. Then it was further purified by silica gel column chromatography (ethyl acetate / hexane...

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Abstract

The invention discloses a method for synthesizing high-selectivity oxaziridine through a chemical enzyme process and belongs to the technical field of chemical synthesis. According to the method, aromatic aldehyde and fatty amine are used as reaction substrates, acetonitrile is used as a solvent and D-ethyl mandelate is used as a peroxy-acid precursor. The method comprises the following operationsteps: adding enzyme, an oxidizing agent, the reaction substrates, the peroxy-acid precursor and the solvent into a reaction container, stirring and reacting for 2 hours under the room-temperature condition to obtain the high-selectivity oxaziridine. The experiment proves that lipase has an obvious catalyzing effect of the reaction and can reach high cis-trans selectivity which is greater than 90%or more; no by-product is generated in the reaction process. Compared with the conventional chemical synthesis method, the method has the advantages of metal-free catalysis, green and environmental protection, low cost, high efficiency and high selectivity; a new method is provided for synthesizing oxaziridine compounds with cis-trans selectivity.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing highly selective oxaziridine by chemical enzymatic method. Background technique [0002] Oxyaziridine is a three-membered heterocyclic organic molecule containing oxygen, nitrogen, and carbon. Its derivatives are usually used as oxidants for different reactions, and have important research value in the field of chemical synthesis. The traditional synthetic method of oxaziridine is chemical method, and traditional chemical method often uses the mode of catalytic imine oxide such as m-chloroperoxybenzoic acid, acetic anhydride, transition state metal to prepare oxaziridine (L.Martiny and K.A. J.Chem.Soc., Perkin Trans.1, 1995, 699.), the reagents used are harmful to the environment and the production process is loaded down with trivial details, and by-products are generated. [0003] Because enzymes have the advantages of mild reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P17/14
CPCC12P17/14
Inventor 王磊张柳李奉熙王智张佳欣
Owner JILIN UNIV
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