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Method for preparing (R)-1-(2-naphthyl) ethylamine through enzymatic resolution

An enzymatic splitting technology of naphthyl, applied in biochemical equipment and methods, enzymes, hydrolytic enzymes, etc., can solve the problems of poor reutilization rate of enzyme catalysts, slow racemization speed of nickel catalysts, etc., and achieve excellent splitting effect , High reusability, good operation stability

Inactive Publication Date: 2019-03-01
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the problems of slow racemization speed of nickel catalyst and poor reuse rate of enzyme catalyst, and improves the reaction rate of racemization catalyst and the reuse rate of Candida antarctica lipase B

Method used

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  • Method for preparing (R)-1-(2-naphthyl) ethylamine through enzymatic resolution
  • Method for preparing (R)-1-(2-naphthyl) ethylamine through enzymatic resolution
  • Method for preparing (R)-1-(2-naphthyl) ethylamine through enzymatic resolution

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Experimental program
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Effect test

Embodiment 1

[0026] The method for preparing (R)-1-(2-naphthyl)ethylamine by chemical enzymatic dynamic kinetic resolution of the present embodiment has the following steps:

[0027] ① First, prepare 50ml of Candida antarctica lipase B (hereinafter referred to as CALB) enzyme solution with a concentration of 3.0mg / mL, add 150mg of epoxy resin Eupergit C to the enzyme solution, stir at 25°C for 3 hours, and remove the resin from the enzyme solution. The solution was separated, washed with pH=7.0 buffer, and dried in vacuum to obtain immobilized CALB (3.0% protein content).

[0028] ②In the reaction system, in 5mL of toluene solvent, add 250mg of immobilized CALB and 2565mg of 1-(2-naphthyl)ethylamine racemate (1.5mmol, hereinafter referred to as racemate) prepared in step ① And 418mg of ethyl 4-nitrophenyl acetate (2.0mmol), immobilized nano palladium (1.56nm, content 4.7%, carrier natural hydrotalcite) 400mg, H 2 The pressure is 0.02MPa, and the reaction is carried out at a constant tempe...

Embodiment 2～7

[0033] The method of each example is basically the same as Example 1, and the differences are shown in Table 1.

[0034] Table 1

[0035]

[0036]

[0037] As can be seen from Table 1, under other conditions being the same, the immobilized nano-palladium with an average particle size of 1.56nm and a palladium content of 4.7% is used as the racemization catalyst, and the immobilized CALB with a protein content of 3.0% is the best.

Embodiment 8～ Embodiment 12

[0039] Each embodiment is basically the same as embodiment 2 (that is, the immobilized nano-palladium hegudingh of embodiment 2 is used), and the differences are shown in Table 2.

[0040] Table 2

[0041]

[0042]

[0043]It can be seen from Table 2 that in the case of using the same immobilized enzyme, the chemical enzyme resolution effect of Example 11 (at a racemization temperature of 90° C. and a hydrogen pressure of 0.02 MPa) is the best. The following control experiment adopts embodiment 11.

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Abstract

The invention relates to a method for preparing (R)-1-(2-naphthyl) ethylamine through a chemical enzymatic method. The method comprises the following steps that nano-palladium is loaded by using hydrotalcite or hydrotalcite-like compounds so as to obtain immobilized palladium; the surface of an epoxy resin carrier is covalently combined with candida antarctica lipase B (CALB) so as to obtain immobilized CALB, the immobilized CALB serves as a catalyst, methylbenzene serves as a solvent, 4-nitrophenyl ethyl acetate serves as an acyl donor, and the (R)-1-(2-naphthyl) ethylamine is selectively esterified; and under the catalysis of the immobilized nano-palladium, (S)-1-(2-naphthyl) ethylamine and hydrogen are subjected to racemization reaction, after the reaction is finished, gas-solid-liquidseparation is carried out. According to the method, the palladium catalyst is immobilized, so that the reuse rate of the palladium catalyst is increased, meanwhile, the candida antarctica lipase B issubjected to covalent immobilization, so that the operation stability of the candida antarctica lipase B is improved.

Description

technical field [0001] The invention relates to a biological resolution method, in particular to a method for enzymatic resolution and preparation of (R)-1-(2-naphthyl)ethylamine. Background technique [0002] (R)-1-(2-naphthyl)ethylamine is an important pharmaceutical intermediate for the synthesis of coronavirus PLpro protease inhibitors; it is also an important raw material for the synthesis of chiral ligands used to catalyze the asymmetric alkylation reaction of aromatic aldehydes; At the same time, it can be used as a chiral base to resolve various acids. Currently, the methods for splitting and preparing (R)-1-(2-naphthyl)ethylamine mainly include chemical and enzymatic methods: [0003] Chemical resolution methods: such as chiral tartaric acid, L-aspartic acid, chiral naproxen reported in scientific research papers, and 6-methoxy-naphthyl glycolic acid (JP 2005060231) reported in Japanese patents. The agent forms a salt with 1-(2-naphthyl)ethylamine racemate, and th...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P13/00C12N11/08
CPCC12N9/20C12N11/08C12P13/001C12P41/001C12Y301/01003
Inventor 汪斌贡洁翁居轼杨凤丽陈舟梁国斌叶招莲刘维桥
Owner JIANGSU UNIV OF TECH
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