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Method for preparing nucleoside polymerase inhibitor PSI-7977 intermediate

A technology of PSI-7977 and nucleoside polymerase, which is applied in the direction of organic chemistry, can solve the problems of low yield, easy polymerization, and difficult preparation, and achieve cheap and easy-to-obtain reaction raw materials, mild reaction conditions, and simple purification Effect

Inactive Publication Date: 2014-09-17
苏州景泓生物技术有限公司
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  • Abstract
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Problems solved by technology

The R-(+)-2,2-dimethyl-1,3-dioxolane-4-formaldehyde used in this method has poor stability, is easy to polymerize, is not easy to prepare, and the yield of the reaction is not high. High, not suitable for industrial production

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  • Method for preparing nucleoside polymerase inhibitor PSI-7977 intermediate
  • Method for preparing nucleoside polymerase inhibitor PSI-7977 intermediate
  • Method for preparing nucleoside polymerase inhibitor PSI-7977 intermediate

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Embodiment Construction

[0037] The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments.

[0038]A method for preparing a nucleoside polymerase inhibitor PSI-7977 intermediate, the first step: adding D-mannitol to a dimethyl sulfoxide solution, stirring at a temperature of 20-30° for 1-30 minutes, adding ring Hexanone, and then add ethyl orthoformate and trifluoroboron ethyl ether solution to the reaction solution, keep the temperature of 20-30° and stir overnight, after the reaction is complete, quench with sodium bicarbonate solution, stir for 20-60 minutes, add Extract with ethyl acetate, wash and dry the organic phase successively with saturated sodium chloride, then depressurize to 20-40Pa in a water bath not higher than 40°, preferably 30Pa to remove the solvent, and the oily liquid is obtained as compound III, D- The mass ratio of mannitol: organic solvent: cyclohexanone: ethyl orthoformate: trifluoroboron ether solution is 1:...

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Abstract

The invention discloses a method for preparing a nucleoside polymerase inhibitor PSI-7977 intermediate. The method comprises the following steps of dissolving a compound X in organic base, dropwisely adding BzCl into the solution at a temperature of -10 to 10 DEG C, carrying out stirring at the constant temperature for 1-3 DEG C, after TLC detection reaction is finished, adding water into the reaction product, carrying out suction filtration after white solids are precipitated, washing the filter cake by water many times, adding DCM into the filter cake for dissolution, carrying out separation water-removal, then carrying out drying and condensation to obtain a crude product, and carrying out crystallization by ethyl acetate and petroleum ether to obtain white solids which are the PSI-7977 intermediates, wherein a mass ratio of the compound X, the organic base, BzCl to water is about 1: 5-25: 1-10: 10-50. Compared with the original route, the method utilizes cheap and easily available raw materials, is stable, has mild reaction conditions, a high yield and simple purification process, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing an intermediate of nucleoside polymerase inhibitor PSI-7977, which belongs to the technical field of organic synthesis. Background technique [0002] According to the World Health Organization (WHO), there are 170 million hepatitis C virus (HCV) carriers worldwide, and the disease kills about 350,000 people every year. However, the development of new drugs for hepatitis C (HC) has entered the fast lane. In 2011, Vertex / Johnson & Johnson's protease inhibitor Incivek (telaprevir) was approved for marketing in the United States and the European Union, and within just 9 months, it gained the status of "blockbuster" (Victrelis of Merck & Co. Previr) is another protease inhibitor approved in 2011). However, the sales volume of Incivek is not out of reach. New drugs of the same kind that will be launched in the next 3 to 4 years are expected to surpass Incivek. Other protease inhibitors that are more promising...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 蔡振伟杨建章
Owner 苏州景泓生物技术有限公司
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