Preparation method of high-purity Ubenimex

A technology of ubimethoxine and high purity, applied in the field of preparation of high-purity ubimethoxine, can solve the problems of expensive condensing agent, unfavorable industrial production, time-consuming 24 hours, etc. Reagent cost, energy saving effect

Active Publication Date: 2016-09-28
SICHUAN QINGMU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The patent describes the advantages of using L-lysine as a resolving agent, but the crystallization time of the resolution step takes more than 24 hours, and the crude product after resolution requires at least two recrystallizations to reach the target purity
And this patent uses EDCI as condensing agent during amide condensation step, and this condensing agent price is more expensive, is unfavorable for industrialized production

Method used

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  • Preparation method of high-purity Ubenimex
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  • Preparation method of high-purity Ubenimex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation method of Ubenimex

[0035] Put 40.0 g of crude ubenimex into 1600 mL of a mixed solution of ethanol and water (volume ratio of water: ethanol = 1:1), and stir evenly. Then heat to an internal temperature of 80°C, keep stirring until the solids are completely dissolved. Stop heating, cool down to 6°C at a constant speed, keep stirring for 30 minutes, and then filter with suction. The filter cake is vacuum-dried at 60°C to obtain a dry weight of 33.0g, a yield of 82.5%, a purity of 99.82%, and a maximum purity of 0.12%.

Embodiment 2

[0036] Embodiment 2: the preparation method of Ubenimex

[0037] Put 10.0g of crude ubenimex into 600mL ethanol aqueous solution (water:ethanol volume ratio=1:1), and stir evenly. Then heat to an internal temperature of 78°C and keep stirring until the solids are completely dissolved. Stop heating, cool down to 8°C at a constant speed, keep stirring for 30 minutes, then suction filter, and vacuum-dry the filter cake at 60°C to obtain a dry weight of 7.75g, a yield of 77.5%, a purity of 99.82%, and a maximum purity of 0.11%.

Embodiment 3

[0038] Embodiment 3: the preparation method of Ubenimex

[0039] Put 10.0g of crude ubenimex into 1000mL ethanol aqueous solution (water:ethanol volume ratio=1:1), and stir evenly. Then heat to an internal temperature of 75°C and keep stirring until the solids are completely dissolved. Stop heating, cool down to 8°C at a constant speed, keep stirring for 30 minutes, and then filter with suction. The filter cake is vacuum-dried at 60°C to obtain a dry weight of 5.42g, a yield of 54.2%, a purity of 99.83%, and a maximum purity of 0.10%.

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Abstract

The invention belongs to the field of medicinal chemical preparation, and particularly relates to a preparation method of high-purity Ubenimex. The method includes the following steps of adding a Ubenimex crude product to a mixed solution of water and other organic solvent to be heated, stirred and dissolved, after dissolving, conducting cooling, crystallizing and suction filtration, and conducting vacuum drying on obtained filter cakes to obtain the final Ubenimex product. By controlling parameters of the preparation method, the yield and purity of Ubenimex can be remarkably improved, product purity is high, and product quality is better ensured.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical preparation, and in particular relates to a method for preparing high-purity ubenimex. Background technique [0002] Ubenimex, its chemical name is: N-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutyryl]-L-leucine; molecular formula: C 16 h 24 N 2 o 4 ; Molecular weight: 308.37; Its structural formula is as follows: [0003] [0004] The patent US4281180 discloses the preparation method of Ubenimex, in which the palladium-carbon hydrogenation reaction is used in the two steps of carbonyl reduction and deprotection of the Ubenimex intermediate, and the two hydrogenation reactions are prone to excessive hydrogenation impurities : In the subsequent process of adding hydrochloric acid to dissolve, and then adding ammonia water dropwise to adjust the pH value to crystallize, the impurity cannot be effectively removed. Therefore, if the hydrogenation reaction is out of control, causing excessive ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/20C07C231/24
CPCC07B2200/07C07C231/24C07C237/20
Inventor 王颖李晓迅卢铁刚刘时奎
Owner SICHUAN QINGMU PHARMA CO LTD
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