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Method for synthesizing L-carnitine by using (R)-(-)-3-chlorine-1,2-propylene glycol as chiral initiative raw material

A technology of propylene glycol and carnitine, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effect of simple reaction conditions and high-efficiency conversion

Inactive Publication Date: 2013-03-13
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no use of the by-product (R)-(-)-3-chloro-1,2-propanediol by-product when L-carnitine is produced by chiral resolution of racemic epichlorohydrin both at home and abroad. Bibliographical reports on preparation of L-carnitine by conversion of sex source as starting material

Method used

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  • Method for synthesizing L-carnitine by using (R)-(-)-3-chlorine-1,2-propylene glycol as chiral initiative raw material
  • Method for synthesizing L-carnitine by using (R)-(-)-3-chlorine-1,2-propylene glycol as chiral initiative raw material
  • Method for synthesizing L-carnitine by using (R)-(-)-3-chlorine-1,2-propylene glycol as chiral initiative raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Put 15.68g (0.142mol) of (R)-(-)-3-chloro-1,2-propanediol and 70ml of dichloromethane into a three-neck flask, stir to dissolve. The temperature was raised to 50° C., and 25.27 g (0.156 mol) of triethyl orthoacetate was added. After reacting for 1 h, the reaction was terminated. Low-boiling substances were evaporated under reduced pressure to obtain 25.74 g of a colorless liquid, which was the intermediate of the cyclic condensate. It was directly used in the next reaction without purification. The yield of the cyclic condensate intermediate was 100%.

[0027] (2) Dissolve 25.74g of the cyclic condensate intermediate prepared in (1) above in 50mL of dichloromethane, add 23.87g (0.156mol) of bromotrimethylsilane, and react for 2 hours, then add 70ml of water to the reaction system , to terminate the reaction. The aqueous layer of the system was extracted twice with dichloromethane, and the organic layers were combined. The organic layer was dried with anhydrous ...

Embodiment 2

[0032] (1) Put 31.4g of (R)-(-)-3-chloro-1,2-propanediol and 130ml of dichloromethane into a three-necked flask, and stir to dissolve. The temperature was raised to 60° C., and 50.5 g of triethyl orthoacetate was added. After reacting for 1 h, the reaction was terminated. Low-boiling substances were evaporated under reduced pressure to obtain 51.5 g of a colorless liquid, which was the intermediate of the cyclic condensation product. It was directly used in the next reaction without purification. The yield of the cyclic condensate intermediate was 100%.

[0033] (2) The 51.5g cyclic condensate intermediate prepared by the above step (1) is dissolved in 100mL of dichloromethane, Add 38.4g acetyl bromide, After reacting for 2 hours, 130ml of water was added to the reaction system to terminate the reaction. The aqueous layer of the system was extracted twice with dichloromethane, the organic layers were combined, and the organic layer was washed with saturated sodium bicarbon...

Embodiment 3

[0038] (1) Put 23.52g of (R)-(-)-3-chloro-1,2-propanediol and 100ml of dichloromethane into a three-necked flask and stir to dissolve. The temperature was raised to 55° C., and 38 g of triethyl orthoacetate was added. After reacting for 1 h, the reaction was terminated. Low-boiling substances were evaporated under reduced pressure to obtain 38.6 g of a colorless liquid, which was the intermediate of the cyclic condensation product. It was directly used in the next reaction without purification. The yield of the cyclic condensate intermediate was 100%.

[0039] (2) The 23.52g cyclic condensate intermediate prepared in the above step (1) was dissolved in 75mL dichloromethane, added 21.7g butyryl bromide After 2 hours of reaction, 100ml of water was added to the reaction system to terminate the reaction. The aqueous layer of the system was extracted twice with dichloromethane, the organic layers were combined, and the organic layer was washed with saturated sodium bicarbonat...

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Abstract

The invention provides a method for synthesizing L-carnitine by using (R)-(-)-3-chlorine-1,2-propylene glycol as a chiral initiative raw material, which belongs to the field of medicament chemistry. The method comprises the following steps of: mixing a side product, namely (R)-(-)-3-chlorine-1,2-propylene glycol used as the initiative raw material with triethyl orthoacetate for reacting to produce an annular condensation compound, wherein the side product is generated when the L-carnitine is prepared by chirally splitting racemic epoxy chloropropane; reacting the annular condensation compound with trimethylsilyl bromide to obtain brominated substance; reacting the brominated substance with sodium cyanide to produce cyanide; reacting the cyanide with trimethylamine to produce ammonium chloride salt; and performing hydrolysis and ion exchange on the ammonium salt under the acidic condition to produce the L-carnitine finally. The method has the advantage that: the L-carnitine is prepared by using the side product, namely (R)-(-)-3-chlorine-1,2-propylene glycol which is generated when the L-carnitine is prepared by chirally splitting racemic epoxy chloropropane as the chiral initiative raw material and by adopting low-cost and readily available chemical raw materials, the reaction condition is simple and mild and the conversion efficiency is high.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a method for synthesizing L-carnitine with (R)-(-)-3-chloro-1,2-propanediol as a chiral starting material, in particular to a A method for synthesizing L-carnitine by using the by-product (R)-(-)-3-chloro-1,2-propanediol as the starting material when preparing L-carnitine from racemic epichlorohydrin. Background technique [0002] L-carnitine also known as carnitine or vitamin B T , the chemical name is (3R)-(-)-3-hydroxy-4-trimethylammonium butyric acid, and the structural formula is: [0003] [0004] L-Carnitine is a very important "conditional nutrient". It has a variety of physiological functions, mainly playing an important role in fat metabolism and energy metabolism. It is widely used in food additives, medicines, animal feed additives, etc. [0005] There are many ways to synthesize L-carnitine, such as relatively mature enzymatic transformation, microbial ferment...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/22C07C227/26
Inventor 杨运旭王伟力
Owner UNIV OF SCI & TECH BEIJING
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