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• W2327571528 endingPage "3635" @default.
• W2327571528 startingPage "3616" @default.
• W2327571528 abstract "The development of a large scale synthesis of the glucocorticoid agonist BI 653048 BS H3PO4 (1·H3PO4) is presented. A key trifluoromethyl ketone intermediate 22 containing an N-(4-methoxyphenyl)ethyl amide was prepared by an enolization/bromine-magnesium exchange/electrophile trapping reaction. A nonselective propargylation of trifluoromethyl ketone 22 gave the desired diastereomer in 32% yield and with dr = 98:2 from a 1:1 diastereomeric mixture after crystallization. Subsequently, an asymmetric propargylation was developed which provided the desired diastereomer in 4:1 diastereoselectivity and 75% yield with dr = 99:1 after crystallization. The azaindole moiety was efficiently installed by a one-pot cross coupling/indolization reaction. An efficient deprotection of the 4-methoxyphenethyl group was developed using H3PO4/anisole to produce the anisole solvate of the API in high yield and purity. The final form, a phosphoric acid cocrystal, was produced in high yield and purity and with consistent control of particle size." @default.
• W2327571528 created "2016-06-24" @default.
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• W2327571528 date "2013-04-01" @default.
• W2327571528 modified "2023-09-26" @default.
• W2327571528 title "Development of a Large Scale Asymmetric Synthesis of the Glucocorticoid Agonist BI 653048 BS H₃PO₄" @default.
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• W2327571528 doi "https://doi.org/10.1021/jo400079z" @default.
• W2327571528 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/23544738" @default.
• W2327571528 hasPublicationYear "2013" @default.
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