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Preparation method of chiral 3-hydroxy-2-butanone

A technology of hydroxyl and butanone, which is applied in the field of preparation of chiral 3-hydroxy-2-butanone, can solve the problems of expensive coenzymes and many by-products, and achieve the effect of cheap, economical and effective preparation methods

Inactive Publication Date: 2019-01-18
张国豪
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, chiral 3-hydroxy-2-butanone is mainly obtained by using metal catalysts to selectively reduce 2,3-butanedione and selectively oxidize 2,3-butanediol, where there is over-reduction or over-oxidation, and There are many by-products, but it is necessary to add expensive coenzymes when using the biological enzyme diacetyl reductase for biocatalysis

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] A preparation method of chiral 3-hydroxyl-2-butanone, comprising the following steps:

[0014] Step 1. Biotransformation: First, weigh (rac)-3-hydroxy-2-butanone (0.5 mmol, 44.0 mg) and dissolve it in an Erlenmeyer flask (specification: 25 mL) filled with 5 mL of methyl tert-butyl ether , then pipetted vinyl chloroacetate (2.5 mmol, 301.3 mg) into the reaction solution with a pipette gun, then weighed commercial lipase Lipozyme 435 (50 mg) as a biocatalyst and added it to the reaction solution, and finally placed the reaction bottle in The reaction was carried out in a shaker at 250 rpm and 30° C. for 12 h.

[0015] Step 2. Detection of biotransformation results: After the above biotransformation is completed, add ethyl acetate for extraction, then filter, spin evaporate to remove the solvent, and separate by column chromatography to obtain (R)-3-hydroxyl-2-butanone with a 50% yield , The product was analyzed by chiral GC, 91%ee.

[0016] Product analysis:

[0017] G...

Embodiment 2

[0020] A preparation method of chiral 3-hydroxyl-2-butanone, comprising the following steps:

[0021] Step 1. Biotransformation: First, weigh (rac)-3-hydroxy-2-butanone (0.5 mmol, 44.0 mg) and dissolve it in an Erlenmeyer flask (specification: 25 mL) filled with 5 mL of methyl tert-butyl ether , then pipetted vinyl chloroacetate (2.5 mmol, 301.3 mg) into the reaction solution with a pipette gun, then weighed commercial lipase Lipozyme TL IM (50 mg) as a biocatalyst and added it to the reaction solution, and finally put the reaction bottle React in a shaker at 250 rpm and 30°C for 12h.

[0022] Step 2. Detection of biotransformation results: After the above biotransformation is completed, add ethyl acetate for extraction, then filter, spin evaporate to remove the solvent, and separate by column chromatography to obtain (R)-3-hydroxyl-2-butanone with a 50% yield , The product was analyzed by chiral GC, 87%ee.

[0023] Product analysis:

[0024] GC detection column model: BGB-...

Embodiment 3

[0027] A preparation method of chiral 3-hydroxyl-2-butanone, comprising the following steps:

[0028] Step 1. Biotransformation: First, weigh (rac)-3-hydroxy-2-butanone (0.5 mmol, 44.0 mg) and dissolve it in an Erlenmeyer flask (specification: 25 mL) filled with 5 mL of methyl tert-butyl ether , then pipetted vinyl chloroacetate (2.5 mmol, 301.3 mg) into the reaction solution with a pipette gun, then weighed commercial lipase Lipozyme RM IM (50 mg) as a biocatalyst and added it to the reaction solution, and finally put the reaction bottle React in a shaker at 250 rpm and 30°C for 12h.

[0029] Step 2. Detection of biotransformation results: After the above biotransformation is completed, add ethyl acetate for extraction, then filter, spin evaporate to remove the solvent, and separate by column chromatography to obtain (R)-3-hydroxyl-2-butanone with a 50% yield , The product was analyzed by chiral GC, 99% ee.

[0030] Product analysis:

[0031] GC detection column model: BGB...

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Abstract

A method for preparing a chiral 3-hydroxy-2-butanone comprises the following steps: biotransformation: firstly weigh 3-hydroxy-2- butanone 44.0 mg in a specification containing 5 mL of bioconversion reaction solvent In a 25 mL Erlenmeyer flask, 301.3 mg of the acyl donor involved in the reaction in the biotransformation was then pipetted into the reaction solution, and then the biocatalyst (50 mg)was weighed into the reaction solution as a biocatalyst. Finally, the reaction flask was reacted in a shaker at 250 rpm and 30 DEG C for 12 h; bioconversion results were detected: after the above bioconversion was completed, ethyl acetate was added for extraction, followed by filtration, rotary evaporation of the solvent, and separation by column chromatography to obtain chirality-3-Hydroxy-2-Butanone, the biotransformation result was detected by a GC instrument. The invention obtains high optical purity, low cost and safety and environmental protection.

Description

technical field [0001] The invention relates to the technical field of biocatalysis and chiral synthesis, in particular to a preparation method of chiral 3-hydroxy-2-butanone. Background technique [0002] Chiral 3-hydroxy-2-butanone is an aroma enhancer for foods such as cream, cheese, coffee and nuts. It is considered to be an important component of the quality of liquor. It can adjust the flavor of liquor and has the effect of increasing flavor. Containing chiral 3-hydroxy-2-butanone, using green biological methods to efficiently obtain highly optically pure 3-hydroxy-2-butanone is still the bottleneck of biotransformation. [0003] At present, chiral 3-hydroxy-2-butanone is mainly obtained by using metal catalysts to selectively reduce 2,3-butanedione and selectively oxidize 2,3-butanediol, where there is over-reduction or over-oxidation, and There are many by-products, but it is necessary to add expensive coenzymes when using the biological enzyme diacetyl reductase fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P41/00
CPCC12P41/004
Inventor 张国豪黄永镇魏家群黄厚今秦磊
Owner 张国豪
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