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Synthesis method of N-methoxycarbonyl group-L-valine

A synthesis method and methoxycarbonyl technology are applied in chemical instruments and methods, preparation of carbamate derivatives, preparation of organic compounds, etc., to achieve the effects of mild reaction temperature, high yield and low cost

Inactive Publication Date: 2016-09-21
NANJING REDWOOD FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Therefore, MOC-L-valine with good quality and low cost has good market value, and there is no report on the synthesis of MOC-L-valine at present.

Method used

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  • Synthesis method of N-methoxycarbonyl group-L-valine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 1,500kg of methanol, 200kg of L-valine, and 50kg of triethylamine into the reaction kettle, and add 410kg of methyl chloroformate dropwise at 60°C, keep the temperature for 12 hours, at a temperature of 40°C, and a pressure of -0.085mpa Concentrate under reduced pressure to a slurry state, then add 1200 kg of water, adjust the pH to 1.5 with hydrochloric acid, crystallize at room temperature for 2 hours, and centrifuge to obtain 260 kg of the product. After testing, purity: greater than 99%; chiral purity: greater than 99.9%.

Embodiment 2

[0026] Add 1800kg of ethanol to the reaction kettle, add 240kg of L-valine, add 60kg of triethylamine, raise the temperature to 63°C, add 490kg of methyl chloroformate dropwise, keep it warm for 13 hours, at a temperature of 43°C and a pressure of -0.085mpa Add 1400kg of water to the concentration, adjust the pH to 1.5 with phosphoric acid, crystallize at room temperature for 2 hours, and centrifuge to obtain 312kg of the product. After testing, the purity is greater than 99%; the chiral purity is greater than 99.9%.

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Abstract

The invention discloses a synthesis method of N-methoxycarbonyl group-L-valine. The synthesis method includes the following steps that methyl alcohol or ethyl alcohol is added into a reaction kettle, L-valine and triethylamine are added in sequence, after the temperature is raised, methylclhlorofonmate is dropwise added into the reaction kettle, after a reaction is completed, decompression, distillation and concentration are conducted till the mixture is made into pulp, then water is added, pH is regulated to 1.0-2.0 with hydrochloric acid or phosphoric acid, crystal separation is conducted, and a product is obtained. The synthesis method is mild in reaction temperature, low in safety coefficient, environmentally friendly and low in cost.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of N-methoxycarbonyl-L-valine. Background technique [0002] N-methoxycarbonyl-L-valine (referred to as MOC-L-valine) is the key intermediate of these antiviral drugs, and there are a large number of pharmaceutical intermediates such as daclatasvir, ledipasvir and velpatasvir Use MOC-L-Valine. [0003] Hepatitis C virus hepatitis C or hepatitis C for short, is a kind of viral hepatitis caused by hepatitis C virus (HCV) infection. According to the statistics of the World Health Organization, the global HCV infection rate is about 3%, with a total of about 180 million people. Approximately 3.2 million people in the United States have hepatitis C. HCV infection mainly includes immune-mediated and HCV direct injury. After infection, the liver becomes inflamed, leading to decreased liver function or even failure. The pathological manifestat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/22
CPCC07C269/04
Inventor 李钢吴法浩高仰哲
Owner NANJING REDWOOD FINE CHEM CO LTD
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