Synthesis method of intermediate compound of sofosbuvir

A synthesis method and intermediate technology, which are applied to the synthesis field of intermediate compounds, can solve the problems of low atom economy, long production cycle, and many three wastes, etc., and achieve the effects of simple and easy synthesis route, low cost and simple steps.
CN104987355AInactive Publication Date: 2015-10-21SHANGHAI TWISUN BIO PHARM
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
SHANGHAI TWISUN BIO PHARM
Publication Date
2015-10-21
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention provides a synthesis method of an intermediate compound of sofosbuvir as shown in formula (I) (see specification). The synthesis method of the intermediate compound of sofosbuvir, a synthetic route of which is as follows: (see specification) the synthesis method comprises the following steps: taking (3R, 4R, 5R)-3-fluoro-dihydro-4-hydroxl3-methyl furan-2(3H)-ketone as an initial raw material to react with pivaloyl chloride to generate an intermediate product (XII); reducing the intermediate product to obtain an intermediate product (XIII); enabling the intermediate product (XIII) to react with pivaloyl chloride to generate an intermediate product (XIV); generating an intermediate product (XV) by virtue of the reaction of the intermediate product (XIV) and a hydrogen bromide; performing silyl-hilbert-johnson reaction for the intermediate product (XV) and uracil to generate an intermediate product (XVI); enabling the intermediate product (XVI) to react with sodium methoxide to obtain a target product. The synthesis method of the intermediate compound (I) is moderate in reaction condition, simple in procedure, low in cost, environment-friendly and favorable for the industrialized production.
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Description

technical field

[0001] The present invention relates to a kind of synthetic method of medicine intermediate, relate in particular to a kind of synthetic method of the intermediate compound of sofosbuvir. Background technique

[0002] Sofosbuvir is an anti-hepatitis C patent drug newly developed by Gilead Sciences of the United States. Its chemical name is: (S)-2-[(((2R,3R,4R,5R)-5-(2,4-di Oxo-3,4-dihydropyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino]propionic acid Isopropyl ester, the structural formula is as follows:

[0003]

[0004] It is the first drug approved for an all-oral treatment regimen for hepatitis C. The product was approved by the US Food and Drug Administration in December 2013 and the European Union in January 2014. Currently, Sofosbuvir is regarded as a breakthrough drug in the treatment of hepatitis C, with a cure rate of over 90%.

[0005] According to the "Hepatitis C Screening and Treatment Guide...

Claims

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