1355049-94-3Relevant articles and documents
Continuous Flow C-Glycosylation via Metal-Halogen Exchange: Process Understanding and Improvements toward Efficient Manufacturing of Remdesivir
Kappe, C. Oliver,Von Keutz, Timo,Williams, Jason D.
, p. 2362 - 2368 (2020)
As remdesivir is the first approved treatment for COVID-19 (SARS-CoV-2), its production is likely to be of vital importance in the near future. Continuous flow processing has been demonstrated as a key technology in the manufacturing of high-volume active pharmaceutical ingredients and is considered for use in this synthetic sequence. In particular, the challenging C-glycosylation of a pyrrolotriazinamine via metal-halogen exchange was identified as a transformation with significant potential benefit, as exemplified by calorimetric analysis of each reaction step. Multiple simplifications of this process were attempted in batch but in general were found to be unfruitful. The five-feed process was then transferred to a flow setup, where specific conditions were found to circumvent solid formation and permit stable processing. Detailed optimization of stoichiometries provided an improvement upon batch conditions with a total residence time of 1 min.
Development of a Large-Scale Cyanation Process Using Continuous Flow Chemistry en Route to the Synthesis of Remdesivir
Badalov, Pavel,Chtchemelinine, Andrei,Gao, Detian,Heumann, Lars,Stevens, Andrew C.,Vieira, Tiago
, p. 2113 - 2121 (2020)
The implementation of cyanation chemistry at manufacturing scales using batch equipment can be challenging because of the hazardous nature of the reagents employed and the tight control of reaction parameters, including cryogenic temperatures, that help t
Intermediate of and preparation method thereof
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Paragraph 0348-0346, (2021/09/08)
The present invention provides an intermediate of Remdesivir and a preparation method therefor. The preparation method has the advantages of low costs, high yield, good product purity, etc. , and can achieve the efficient synthesis of Remdesivir. In each formula, R1, R2, R3, R4, R5, R8, PG and X are as defined in the description.
Synthesis method of key intermediate of ridecevir
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Paragraph 0059-0061, (2021/08/07)
The invention provides a novel method for preparing a key intermediate of ridecevir as shown in a formula (VII). Benzyl fully-protected lactone as shown in a formula (I) is used as a starting material and is subjected to ring opening to obtain a compound as shown in a formula (II). The hydroxyl of the compound (II) is protected by a proper protecting group to obtain the compound shown in the formula (III). The compound (III) and the compound (IV) are subjected to coupling, protecting group removal and cyclization to obtain an intermediate shown as a formula (V) by a one-pot method. The intermediate (V) is subjected to two-step conversion to obtain the key intermediate (VII) of the ridecevir. According to the method provided by the invention, the compound (I) which can be bought in the market is used as the starting material, and the key intermediate compound (VII) for preparing the ridecevir is obtained at high yield through five-step reaction, so that the cost is greatly reduced, and the method is suitable for industrial mass production.