A facile deprotection of secondary acetamides.
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.
Koenig
Stefan G
SG
Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, USA. stefan.koenig@sepracor.com
Vandenbossche
Charles P
CP
Zhao
Hang
H
Mousaw
Patrick
P
Singh
Surendra P
SP
Bakale
Roger P
RP