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Synlett 1996; 1996(6): 517-518
DOI: 10.1055/s-1996-5503
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A Facile Synthesis of a Sterically Congested Amide: A Convenient Method of Steroidal 17β-Amide Synthesis from 17β-Carboxylic Acid and a Hindered Amine with 2,4,6-Triisopropylbenzenesulfonyl Chloride as a Condensing Reagent

Hitoshi Kurata, Koki Ishibashi, Koichi Kojima*
  • *Medicinal Chemistry Research Laboratories Sankyo Co. Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140, Japan
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Publication History

Publication Date:
31 December 2000 (online)

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Steroidal 17β-amides 2, 4, 6 were synthesized from the 17β-carboxylic acids 1, 3, 5 and sterically hindered amine in 88-100% yields using 2,4,6-triisopropylbenzenesulfonyl chloride as a condensing reagent. This method was successfully applied to the synthesis of sterically congested simple amide 8.

congested amide - condensation - triisopropylbenzenesulfonyl chloride - steroid

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