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Please login to access the full content or check if you have access via1.2.3.1.5.3 Synthesis of (±)-Bicalutamide through a “Truncated” Passerini Reaction
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Riva, R.; Banfi, L.; Basso, A., Science of Synthesis: Multicomponent Reactions, (2014) 1, 407.
An innovative application of multicomponent reactions is in the field of generic drug synthesis as a support for the pharmaceutical industry.[178] An example is represented by the two-step synthesis of racemic bicalutamide (178), marketed as Casodex, which is a nonsteroidal antiandrogen used for treatment of prostate cancer. The synthesis starts from commercially available 1-[(4-fluorophenyl)sulfanyl]propan-2-one, which is submitted to oxidation affording sulfone 177 (Scheme 72). The following titanium(IV) chloride mediated multicomponent reaction directly gives, upon hydrolysis, 178 with a satisfactory overall yield of 66%. This is not yet an industrial application, because further experiments have to be done to determine if this approach is suitable for scaleup.
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References
| [178] | Meeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meee, M.; Meeeeee, M.; Meee, M., Mee. Meeeeeeee, (8888) 88, 888. |
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