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A process for the production of carnitine from [beta] -lactones

A technology of lactone and carnitine, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of easy change, low yield, time consumption, etc.

Inactive Publication Date: 2013-03-27
LONZA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this reaction is a two-step reaction, thus relatively high labor and time consuming
Furthermore, multistep reactions are often more variable and associated with relatively low yields

Method used

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  • A process for the production of carnitine from [beta] -lactones
  • A process for the production of carnitine from [beta] -lactones
  • A process for the production of carnitine from [beta] -lactones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of β-lactone

[0068] TMSQ catalyst (see scheme 2b above)) was prepared according to the method of Michael A. Calter, J. Org. Chem. 1996, 61, 8006-8007. This catalyst is used in the following [2+2] cycloaddition reaction. In a 500 ml double-jacketed reactor (equipped with overhead stirrer, cryostat for cooling, nitrogen inlet; ketene dip tube) under a nitrogen atmosphere, fill a dichloromethane solution of dichloromethane and chloroacetaldehyde (10.0 g Chloroacetaldehyde dissolved in 135 g DCM). The solution was cooled to -50°C, followed by the addition of 5.16g TMS quinine (dissolved in 55.17g dichloromethane) and 4.09g LiClO 4 (dissolved in 54.1 g DCM and 18.0 g THF). The enone was bubbled through the solution (7 g / h) for 2 hours. The reaction was followed by inline IR (characteristic wavenumber of the product around 1832). The reaction was quenched with saturated aqueous bicarbonate solution (579.1 g). After layer separation, the org...

Embodiment 2

[0069] Embodiment 2: the conversion of reaction product to L-carnitine

[0070] The crude product was added to NaOH and TMA aqueous solution (water 95.0 g, NaOH 7.3 g, TMA 45% in water 20.8 g) at 0°C. The reaction was stirred at this temperature for 1 hour and allowed to warm to room temperature. Stirring was continued for 1 hour. HPLC and IC demonstrated 40% conversion to carnitine (more than two steps), and the composition of L-carnitine was 85.5.

Embodiment 3

[0071] Example 3: Reaction in a two-phase system

[0072] 4-(Chloromethyl)oxetan-2-one (10 wt% in the organic solvent dichloromethane or toluene) was treated with a mixture of 2.5 equivalents of TMA (10-40 wt% in water) and 1.2-1.4 equivalents of NaOH . A biphasic reaction at 0°C followed by a 1 h reaction at room temperature yielded about 30% yield of L-carnitine (over two steps, dissolved in the aqueous phase) and the L-carnitine content was detected to be 85% %. The main by-product is hydroxycrotonic acid.

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PUM

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Abstract

The invention relates to a method for the production of L-carnitine, wherein a [beta] -lactone, which is a 4-(halomethyl)oxetane-2-one, is converted into carnitine with trimethylamine (TMA), wherein the [beta] -lactone is not subjected to a basic hydrolysis step before being contacted with the trimethylamine. The invention also relates to a carnitine having a unique impurity profile.

Description

technical field [0001] The present invention relates to a process for the production of L-carnitine and L-carnitine with a unique impurity profile. Background technique [0002] Carnitine (vitamin Bt: 3-hydroxy-4-trimethylammonium-butyric acid methyl ester) is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. In living cells, fatty acids are required to be transported from the cytoplasm to the mitochondria during the breakdown of phospholipids used to generate metabolic energy. Used as a nutritional supplement. Carnitine exists in two stereoisomers. The biologically active form is L-carnitine, while its enantiomer, D-carnitine, is biologically inactive. When producing L-carnitine in an industrial process, it is desirable to produce the biologically active L-form in high purity. [0003] Various methods for the industrial production of L-carnitine are described herein. In known microbial methods, L-carnitine is produced directly by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/12C07C227/08C07C227/18C07C229/22
CPCC07C229/22C07C227/08C07D305/12C07C227/42C07C227/40C07C227/18
Inventor P·哈泽尔曼E·克莱格拉夫
Owner LONZA LTD
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