A facile deprotection of secondary acetamides

…, CP Vandenbossche, H Zhao, P Mousaw…

Index: Koenig, Stefan G.; Vandenbossche, Charles P.; Zhao, Hang; Mousaw, Patrick; Singh, Surendra P.; Bakale, Roger P. Organic Letters, 2009 , vol. 11, # 2 p. 433 - 436

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Citation Number: 25

Abstract

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.

~75%

~48%

~86%

~58%

~84%

~81%

~86%

~48%

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