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Preparation method for daclatasvir

A technology for daclatasvir and a compound is applied in the field of preparation of daclatasvir, and can solve the problems of cumbersome steps, low economy, low production efficiency and the like

Inactive Publication Date: 2017-10-10
SHANGHAI INST OF PHARMA IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The technical problem to be solved in the present invention is to overcome the high cost, cumbersome steps, relatively harsh reaction conditions, low production efficiency, unfriendly to the environment, low economic efficiency and low cost in the synthetic method of daclatasvir in the prior art. It is suitable for defects such as industrialized production, and a preparation method of daclatasvir is provided

Method used

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  • Preparation method for daclatasvir
  • Preparation method for daclatasvir
  • Preparation method for daclatasvir

Examples

Experimental program
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Effect test

Embodiment 1

[0077] Take L-proline (2g, 0.017mol) in a single-necked bottle, add 20mL of methanol, control the temperature below 0°C, and slowly add SOCl 2 (2.48g, 0.021mol), gradually returned to room temperature and reacted overnight, and TLC detected that the reaction was complete. Concentrate under reduced pressure to obtain an oily substance, which is compound D1, which is directly used for the next reaction.

Embodiment 2

[0079] Take Moc-L-valine (3.04g, 17.4mmol), EDC.HCl (4.01g, 20.9mmol), HOBt (3.19g, 20.9mmol) and acetonitrile (30ml) in a reaction flask, and stir for 1h. Compound D1 prepared in Example 1 was added, and triethylamine (4.39 g, 43.4 mmol) was slowly added dropwise under ice-cooling, and reacted for 18 h, and the reaction was complete as detected by TLC. Add brine (3ml), stir at 50°C for 5h, cool to room temperature, extract with EA and water, and the organic layer is sequentially washed with dilute NaHCO 3 Solution, water and dilute brine were washed, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column to obtain 4.803 g of compound D3, with a two-step yield of 96.5%.

Embodiment 3

[0081] Get 4.8g of compound D3 prepared in Example 2 in a 500mL eggplant-shaped bottle, add 50mL THF, dissolve the product in 5mL water, add 1.27g LiOH·H 2 O. The reaction was carried out at room temperature overnight, and TLC detected that the reaction was complete. Extracted with EA and water, the organic layer was washed successively with dilute HCl solution, water and dilute brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain compound D8, which was put into the next step reaction.

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Abstract

The invention discloses a preparation method for daclatasvir. The preparation method comprises the following steps: in a solvent, performing a cyclization reaction on a compound shown as a formula D10 and ammonium acetate, so as to prepare the daclatasvir shown as a formula I, wherein the cyclization reaction is shown in the description. The preparation method for daclatasvir is low in cost, high in yield, friendly to environment, simple in steps, mild in reaction conditions and suitable for industrialized production.

Description

technical field [0001] The invention specifically relates to a preparation method of daclatasvir. Background technique [0002] Hepatitis C viral hepatitis, referred to as hepatitis C, hepatitis C, is a liver disease caused by hepatitis C virus (hepatitis virus C, HCV), and HCV is one of the most common viruses that infect the liver. According to the statistics of the World Health Organization, there are about 185 million HCV-infected patients in the world, and about 3 million new people are added every year, of which 70-85% develop chronic hepatitis, which in turn leads to liver cirrhosis and hepatocellular carcinoma. [0003] Although hepatitis C virus (HCV) is known to be a major cause of chronic liver disease, there is currently no vaccine to prevent HCV infection. The current standard of care treatment regimen for HCV infection involves the use of interferon-alpha alone or in combination with ribavirin. The treatment is cumbersome and has debilitating or other serious...

Claims

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Application Information

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IPC IPC(8): C07D403/14
CPCC07D403/14
Inventor 林峰杨永全陈建丽李莉张红亮赵源
Owner SHANGHAI INST OF PHARMA IND
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