A facile deprotection of secondary acetamides.

Org Lett

Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, USA.

Published: January 2009

Imidoyl chlorides, generated from secondary acetamides and oxalyl chloride, can be harnessed for a selective and practical deprotection sequence. Treatment of these intermediates with 2 equiv of propylene glycol and warming enables the rapid release of amine hydrochloride salts in good yields. Notably, the reaction conditions are mild enough to allow for a swift deprotection with no observed epimerization of the amino center.

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http://dx.doi.org/10.1021/ol802482dDOI Listing

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