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A Facile Deprotection of Secondary Acetamides

Stefan G. Koenig*, Charles P. Vandenbossche, Hang Zhao, Patrick Mousaw, Surendra P. Singh and Roger P. Bakale

*Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, Email: stefan.koenigsepracor.com

S. G. Koenig, C. P. Vandenbossche, H. Zhao, P. Mousaw, S. P. Singh, R. P. Bakale, Org. Lett., 2009, 11, 433-436.

DOI: 10.1021/ol802482d (free Supporting Information)


Abstract

Imidoyl chlorides, generated from secondary acetamides and oxalyl chloride, enable a selective and practical deprotection sequence. Treatment of these intermediates with propylene glycol enables the rapid release of amine hydrochloride salts in good yields without epimerization of the amino center. The hydrochloride salts can be isolated or carried forward for subsequent chemistry.

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Key Words

Acetamides, Phthalimides


ID: J54-Y2009-0280