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Preparation for sofosbuvir key intermediate

A -2-C-, methyl technology, applied in the field of preparation of key intermediates of sofosbuvir, can solve the problems of dark color of wastewater, long route, excessive oxidation and so on

Inactive Publication Date: 2016-03-23
WISDOM PHARM CO LTD
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  • Abstract
  • Description
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Problems solved by technology

[0008] Although the industrialization route described above has the advantages of cheap raw materials, easy operation, and high yield, it has defects such as long route and difficult treatment of three wastes (the second step uses high Potassium manganate or sodium permanganate double hydroxylation reaction, and use SOCl2 when preparing formula IV from formula III, the amount of waste water is large, and the waste water in some steps is dark in color and difficult to handle)
At the same time, the dihydroxylation step of permanganate oxidation is prone to excessive oxidation, and the yield of the step is not high

Method used

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  • Preparation for sofosbuvir key intermediate
  • Preparation for sofosbuvir key intermediate
  • Preparation for sofosbuvir key intermediate

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Embodiment example

[0019] 1. Reaction formula

[0020]

[0021] 250mL four-necked flask, under magnetic stirring, add ethanol (60mL) and benzonitrile (4mL), start stirring and add potassium carbonate (8.1g, 58.6mol), the system temperature is cooled with ice water, and then slowly add 35%H 2 O 2 (76mL). then slowly add II (8.5g, 39.7mmol) in ethanol (40mL) was added to control the reaction temperature below 0°C. After the dropwise addition was complete, stir at a temperature below 0 °C until TLC showed the disappearance of the starting material. Water (30 mL) was added to the reaction system to quench the reaction, and ethyl acetate (100 mL) was added to the system to stir, and the layers were separated after standing, and the organic phase was separated. The aqueous phase was further extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, and the organic phases were sequentially washed with 5% Na 2 SO 3 It was washed with aqueous solution (50 mL) and saturated br...

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Abstract

The invention relates to preparation for a sofosbuvir key intermediate. With (E)-(S)-3-(2,2-dimethyl-1,3-dioxolane-4-base)-2-ethyl methacrylate being an initial raw material, preparation of 3,5-bis-O-benzoyl-2-deoxidation-2-fluorine-2-C-methyl-D-riboic acid-gamma-lactone is achieved through an epoxidation reaction, fluoridation, a de-acetonylidene cyclization reaction and a benzoyl reaction. According to the method, a synthesis route is short, and in the reaction process, a reagent that oxidability is high, and in the aftertreatment process, potassium permanganate or sodium permanganate and high-corrosivity SOCl2 deep in waste water color will generate a lot of waste water will not be involved.

Description

technical field [0001] The present invention relates to sofosbuvir key intermediate 3,5-bis- O -Benzoyl-2-deoxy-2-fluoro-2- C - Preparation of methyl-D-ribo-γ-lactone. Background technique [0002] Sofosbuvir (also translated as Sofosbuvir, English name Sofosbuvir, trade name Sovaldi, alias GS-7977, PSI-7977) is a new drug developed by Gilead Sciences for the treatment of chronic hepatitis C. The drug is the first to safely and effectively treat certain types of hepatitis C without the need for interferon. Clinical trials have confirmed that for hepatitis C types I and IV, the overall sustained virological response rate (SVR) of the drug combined with peginterferon and ribavirin is as high as 90%; for hepatitis C type II, the drug combined with ribavirin The SVR of the drug is 89%-95%; for type III hepatitis C, the SVR of the drug combined with ribavirin is 61%-63%. The drug was approved by the US FDA in December 2013 for marketing in the United States, and in January 20...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 邹平胡林邱小龙王东辉邓贤明游正伟江中兴
Owner WISDOM PHARM CO LTD
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