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Method for preparing chiral alcohol by using reaction system containing ionic liquid

A reaction system, ionic liquid technology, applied in the field of biocatalysis preparation, can solve the problems of unfriendly environment, non-renewable, poor biodegradability and so on

Active Publication Date: 2014-04-02
扬州市冠科科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional imidazole and pyrimidine ionic liquids have disadvantages such as being environmentally unfriendly, poorly biodegradable, and non-renewable (Chem Soc Rev, 2011, 40:1383)

Method used

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  • Method for preparing chiral alcohol by using reaction system containing ionic liquid
  • Method for preparing chiral alcohol by using reaction system containing ionic liquid
  • Method for preparing chiral alcohol by using reaction system containing ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 4

[0052] The synthesis of embodiment 1 tetramethylammonium glutamic acid ionic liquid

[0053] (1) Resin pretreatment

[0054] Put 1.2Kg201×7 type anion exchange resin in a beaker, add 1L of saturated saline to seal and soak for 24 hours, rinse it with distilled water, and then soak it in 5wt% sodium hydroxide aqueous solution with 4 times the volume of the resin for 4 hours to make it All converted into OH type, rinse the resin with distilled water until neutral.

[0055] Then soak the resin with 5wt% hydrochloric acid aqueous solution of 4 times the volume of the resin for 4 hours to make it all turn into Cl type, pour off the acid solution, and rinse the resin with distilled water until it is neutral.

[0056] Repeat the above operation 1 to 2 times (the purpose is to fully remove the impurity ions contained in the resin), and finally soak the resin with 5wt% sodium hydroxide aqueous solution of 6 times the volume of the resin for 4 hours, so that it is all converted into OH...

Embodiment 2-6

[0062] Tetramethylammonium is replaced with tetrapropylammonium, dimethyldiethylammonium, trimethylethylammonium and tetrabutylammonium respectively in embodiment 1, and glutamic acid is replaced with tyrosine, tyrosine respectively in embodiment 1. Methionine and arginine were replaced to obtain the ionic liquids described in Examples 2-6, respectively.

Embodiment 2

[0063] Embodiment 2: Tetrapropylammonium glutamic acid ionic liquid ([N 3,3,3,3 ] + [Glu] – ), Example 3: Dimethyldiethylammonium tyrosine ionic liquid ([N 1,1,2,2 ]+ [Tyr] – ), Example 4: tetramethylammonium methionine ionic liquid ([N 1,1,1,1 ] + [Met] – ), Example 5: trimethylethylammonium arginine ionic liquid ([N 1,2,1,1 ] + [Arg] – ), Example 6: tetrabutylammonium glutamate ionic liquid ([N 4,4,4,4 ] + [Glu] – ).

[0064] The tetrapropylammonium glutamic acid ionic liquid that embodiment 2 prepares: 1 H NMR (400MHz,D 2 O)δ=3.50(q,1H),2.36(q,8H),2.08(q,4H),1.65(m,2H),1.33(q,8H),0.96(t,12H);

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Abstract

The invention discloses a method for preparing (R)-[3,5-bi(trifluoromethyl) phenyl]ethanol in a reaction system containing ionic liquid. The method comprises the following steps: with wet mycelium obtained by cultivation of trichoderma asperellum ZJPH0810 as a catalyst and 3,5-bi(trifluoromethyl) hypnone as a substrate, reacting for 6-50 hours under the conditions of 25-45 DEG C and 100-300r / min inside the reaction system composed of amino acid ionic liquid shown in a formula (I) and a phosphate buffer of which the pH value is 5.5-8.0; and separating and purifying the reaction liquid to obtain the product (R)-[3,5-bi(trifluoromethyl) phenyl]ethanol. The amino acid ionic liquid disclosed by the invention has the function of facilitating coenzyme regeneration, and is low in toxicity, green and environment-friendly, renewable and biodegradable; the reaction system containing the ionic liquid is applied to biological catalytic reaction, so that the method is friendly to the environment, and accords with the green development strategy, and the defects that the traditional ionic liquid is poor in biodegradability, nonrenewable and the like can be overcome.

Description

(1) Technical field [0001] The invention relates to a biocatalytic preparation method of (R)-3,5-bistrifluoromethylphenylethanol, in particular to a method for improving the preparation of aprepitant by microbial cell catalysis using a reaction system containing amino acid ionic liquids Methods for the efficiency of the reaction of the chiral intermediate (R)-3,5-bistrifluoromethylphenethyl alcohol. (2) Background technology [0002] (R)-3,5-Bistrifluoromethylphenethyl alcohol is a key chiral intermediate in the synthesis of aprepitant, an NK-1 receptor antagonist, for the treatment of chemotherapy-induced nausea and vomiting. Compared with the chemical method, the preparation of (R)-3,5-bistrifluoromethylphenethyl alcohol by microbial cell-catalyzed asymmetric reduction of latent chiral 3,5-bistrifluoromethylacetophenone has mild reaction conditions and selectivity Many advantages. Based on the inventor's original invention "Trichoderma aculeatus and its application in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/22C12R1/885
Inventor 王普李军黄金孙佳孙婧
Owner 扬州市冠科科技有限公司
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