A kind of method for synthesizing oxaziridine by chemical enzymatic method

A technology of oxaziridine and chemical enzymatic method is applied in the field of chemical enzymatic synthesis of oxaziridine, which can solve the problems of environmental harm, complicated production process, and by-products, etc.

Active Publication Date: 2021-05-25
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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  • A kind of method for synthesizing oxaziridine by chemical enzymatic method
  • A kind of method for synthesizing oxaziridine by chemical enzymatic method
  • A kind of method for synthesizing oxaziridine by chemical enzymatic method

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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 / hexa...

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Abstract

The invention discloses a method for synthesizing oxaziridine by chemical enzymatic method, belonging to the technical field of chemical synthesis, using aromatic aldehydes and aliphatic amines as reaction substrates, acetonitrile as a solvent, and ethyl D-mandelate as a peroxyacid precursor . The operation steps include adding enzyme, oxidant, reaction substrate, peroxyacid precursor, and solvent into a reaction vessel, and stirring and reacting at room temperature for 2 hours. It is proved by experiments that the lipase has a significant catalytic effect on the reaction, and can achieve a high cis-trans selectivity of more than 90%, and no by-products are generated during the reaction. Compared with traditional chemical synthesis methods, the method of the present invention has the advantages of metal-free catalysis, environmental protection, low cost, high efficiency, high selectivity, etc., and provides a new method for synthesizing oxaziridine compounds with cis-trans selectivity. train of thought.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing 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 cumbersome and has by-products. [0003] Because enzymes have the advantages of mild reaction conditions, high catalytic activity, and en...

Claims

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Application Information

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Patent Type & Authority Patents(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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