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A kind of preparation method of highly optically pure l-carnitine

An optical and L-carnitine technology, applied in chemical instruments and methods, preparation of organic compounds, cyanide reaction preparation, etc., can solve the problems of not being able to obtain high optical pure L-carnitine products, increasing process costs, and cumbersome operations, etc. Achieve the effect of being suitable for large-scale industrial production, low cost and low emission

Active Publication Date: 2017-12-26
BENGBU BBCA MEDICINE SCI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process needs to prepare ruthenium metal ligand, and the operation is loaded down with trivial details, has increased process cost, and the ee value of the obtained (R)-(-)-4-halogen-3 hydroxybutyric acid alkyl ester intermediate only reaches 96%, still Unable to obtain highly optically pure L-carnitine products

Method used

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  • A kind of preparation method of highly optically pure l-carnitine
  • A kind of preparation method of highly optically pure l-carnitine
  • A kind of preparation method of highly optically pure l-carnitine

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Embodiment 14

[0041] The preparation of embodiment 14-chloro-hydroxybutyric acid ethyl ester

[0042] At 40°C, 45g (1.19mol) of sodium borohydride was dispersed into 500ml of dried tetrahydrofuran, and stirred for 1h. Dissolve 165g (1mol) of ethyl 4-chloro-acetoacetate in 100ml of tetrahydrofuran and add dropwise to the above sodium borohydride dispersion for about 1 hour. After the dropwise addition, keep stirring for 1 hour. After cooling to room temperature, 200 ml of 5% hydrochloric acid solution was added, and tetrahydrofuran was distilled under reduced pressure. The residue was extracted three times with 300 ml of ethyl acetate, and the combined organic layers were washed with saturated ammonium chloride solution until neutral. Add anhydrous magnesium sulfate for drying, remove the desiccant, and distill ethyl acetate under reduced pressure to obtain 150 g of oily liquid ethyl 4-chloro-hydroxybutyrate with a content of 98% (GC) and a yield of 90%.

Embodiment 2

[0043] The preparation of embodiment 2 (R)-4-chloro-hydroxybutyric acid ethyl ester compound

[0044] 16.7g (100mmol) of ethyl 4-chloro-hydroxybutyrate and 8.3g (80mmol) of methyl methoxyacetate prepared in Example 1 were dissolved in 400ml of methyl tert-butyl ether, and then 7.0g of Novozym435 was added, At room temperature, the reaction was shaken for 7h. After the reaction, the immobilized enzyme was filtered off, and the filtrate was evaporated to dryness to obtain an oily residue. The residue was passed through a silica gel column and eluted with ethyl acetate. First, the ethyl acetate solution of (R)-4-chloro-hydroxybutyric acid ethyl ester was collected, and then (S)-4-chloro-hydroxybutyrate was collected. The ethyl acetate solution of ethyl acetate was evaporated to dryness under reduced pressure respectively to obtain 11.8 g of (R)-4-chloro-hydroxybutyric acid ethyl ester esterified product, content 99%, yield 48.7%, (S)-4-chloro- -Ethyl hydroxybutyrate 8.1g, conte...

Embodiment 3

[0045] The preparation of embodiment 3L-carnitine

[0046] Add 11.8g (49mmol) of the esterified product obtained in Example 2, 35g (154mmol) of trimethylamine aqueous solution (26%) and 35mL of ethanol into the reaction flask, and stir the reaction mixture at about 80°C for 5h, then cool to room temperature. Ethanol and unreacted trimethylamine were removed by pressure steaming. Add 50ml of 10% hydrochloric acid to the residue, reflux for 4h, evaporate 50ml of water under reduced pressure, add 55mL of isopropanol to the obtained residue for recrystallization, filter to obtain a white solid. The white solid was dissolved in water and desalted with 732-type cation exchange resin to obtain about 6.5 g of L-carnitine with a content of 99% (HPLC), a yield of 82.4%, and an ee value of 99.3%, [α] 2 D =-30 (c=1, H 2 o).

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Abstract

The invention provides a preparation method of highly optically pure L-carnitine, comprising step 1): taking ethyl 4-chloroacetoacetate as a raw material, and obtaining ethyl 4-chloro-3-hydroxybutyrate through hydroboration reduction reaction; Step 2): Using ethyl 4-chloro-3-hydroxybutyrate obtained in step 1) as the reaction starting material, under the catalysis of immobilized lipase, carry out asymmetric esterification reaction with acyl donor to obtain (R )‑4‑chloro‑3‑hydroxybutyrate ethyl ester and (S)‑4‑chloro‑3‑hydroxybutyrate ethyl ester; step 3): (R)‑4‑chloro‑3‑hydroxybutyrate obtained in step 2) 3-Hydroxybutyrate ethyl ester is the reaction starting material, and after condensation with trimethylamine, the hydrolysis reaction is carried out to obtain L-carnitine. In the preparation method provided by the invention, the reaction raw materials are easy to obtain, the product yield is high, the optical purity is high, by-products can be recycled, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of compound L-carnitine, L-carnitine. Background technique [0002] L-carnitine is L-3-hydroxy-4-trimethylammonium butyric acid, also known as vitamin BT, the structural formula is: [0003] [0004] Molecular formula: C 7 h 15 NO 3 [0005] Molecular weight: 161.20 [0006] L-carnitine is a natural chiral compound existing in living organisms. It is considered as a "vitamin-like" nutrient. It can participate in many metabolic processes of the human body and is an essential substance for fat oxidation and metabolism in the body. Its most prominent physiological function It is the carrier of fatty acid transport. L-carnitine has a wide range of applications. It can be used as a clinical drug for the treatment of chronic renal failure, cardiomyopathy, coronary heart disease, organic acidemia and other diseases. It can also be used as a funct...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/00C12P7/62C07C229/22C07C227/18
Inventor 孙建华张亚徐斌
Owner BENGBU BBCA MEDICINE SCI DEV
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