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Synthesis process of MOC-L-valine

A technology of MOC-L-, synthesis process, applied in the field of MOC-L-valine synthesis process, can solve the problem of irritating odor and the like

Pending Publication Date: 2022-07-01
GENCHEM & GENPHARM CHANGZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Since the above processes all use methyl chloroformate, it has a pungent smell and is a regulated highly toxic and dangerous chemical

Method used

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  • Synthesis process of MOC-L-valine
  • Synthesis process of MOC-L-valine
  • Synthesis process of MOC-L-valine

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Put 110g of water and 40g of liquid caustic soda with a mass fraction of 32% into a 500ml four-necked bottle, turn on stirring, control the temperature of the kettle to be no higher than 20°C, put in 35g of L-valine, and stir until all the solids are dissolved. The internal temperature of the reaction kettle was controlled to be 5-20°C, and 56.9 g of N-succinimidyl methyl carbonate was added in batches at the same time. After the feeding was completed, the internal temperature of the reaction kettle was controlled to be 50-60°C, and the temperature was maintained and stirred for 2-3 hours. Sampling in the control, requires L-valine ≤ 2%. Add 160 g of toluene to the reaction solution, cool down to below 15°C, dropwise add sulfuric acid to adjust pH=2~3, a large amount of solid salt does not dissolve, be warming up to 23~28°C and stir the salt to dissolve completely, separate the water layer to obtain the organic layer. The organic layer was washed three times with 15% br...

Embodiment 2

[0037] Put 110g of water and 53g of sodium carbonate into a 500ml four-necked bottle, turn on stirring, control the temperature of the kettle to be no higher than 20°C, put in 35g of L-valine, and stir until all the solids are dissolved. The internal temperature of the reaction kettle was controlled to be 5-20°C, and 56.9 g of N-succinimidyl methyl carbonate was added in batches at the same time. After the feeding was completed, the internal temperature of the reaction kettle was controlled to be 10-20°C, and the temperature was kept and stirred for 2-3 hours. Sampling in the control, requires L-valine ≤ 2%. Add 160 g of ethyl acetate to the reaction solution, cool down to below 15°C, dropwise add sulfuric acid to adjust pH=2~3, a large amount of solid salt does not dissolve, be warming up to 23~28°C and stir the salt to dissolve completely, separate the water layer to obtain the organic layer . The organic layer was washed with 15% brine, and the internal temperature was con...

Embodiment 3

[0039]Put water 110g and sodium bicarbonate 84g into a 500ml four-neck flask, turn on stirring, control the temperature of the kettle to be no higher than 20°C, put in 35g of L-valine, and stir until all the solids are dissolved. The internal temperature of the reaction kettle was controlled to be 5-20°C, and 56.9 g of N-succinimidyl methyl carbonate was added in batches at the same time. After the feeding was completed, the internal temperature of the reaction kettle was controlled to be 10-20°C, and the temperature was kept and stirred for 2-3 hours. Sampling in the control, requires L-valine ≤ 2%. Add 160 g of tetrahydrofuran to the reaction solution, cool down to below 15°C, dropwise add sulfuric acid to adjust pH=2~3, a large amount of solid salt does not dissolve, heat up to 23~28°C and stir the salt to dissolve completely, separate the water layer to obtain the organic layer. The organic layer was washed with 15% brine, and the internal temperature was controlled not to...

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Abstract

The invention relates to the technical field of organic synthesis of medical intermediates, in particular to a synthesis process of MOC-L-valine, which comprises the following steps: sequentially adding water and an acid-binding agent into a reaction kettle, starting stirring, controlling the kettle temperature to be not higher than 20 DEG C, adding L-valine, and stirring until the solid is completely dissolved; the temperature in the reaction kettle is controlled to be 5-20 DEG C, N-succinimido methyl carbonate is added in batches under stirring, the temperature is controlled, the reaction is finished when L-valine is smaller than or equal to 2%, after the reaction is finished, a solvent is added, acid adjustment, layering, washing and concentration are performed, and the target product MOC-L-valine is obtained through crystallization and separation. Compared with the prior art, the method has the characteristics of safety, environment friendliness, mild reaction conditions, easiness in operation and high purity of the prepared product, and is suitable for industrial mass production.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a synthesis process of MOC-L-valine. Background technique [0002] MOC-L-valine is the abbreviation of (S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid, CAS: 74761-42-5, the chemical structure is as follows: [0003] [0004] MOC-L-valine is a key intermediate of the antiviral drugs Daclatasvir, Ledipasvir, Velpatasvir, etc. [0005] Hepatitis C is a viral disease that can cause inflammation of the liver, leading to reduced liver function or liver failure. Most people infected with hepatitis C have no symptoms until liver damage becomes apparent. Globally, genotype 3 hepatitis C is the second most common genotype after genotype 1 hepatitis C and is considered one of the most difficult genotypes to treat. [0006] Daclatasvir is a pan-genotype NS5A replication complex inhibitor with dual antiviral effects of inhibiting RNA replication and virus as...

Claims

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Application Information

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IPC IPC(8): C07C269/04C07C271/22
CPCC07C269/04C07C271/22
Inventor 王玉琴刘文庆詹玉进
Owner GENCHEM & GENPHARM CHANGZHOU CO LTD
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