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Updated: Jun 26, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
A facile deprotection of secondary acetamides
Stefan G Koenig1, Charles P Vandenbossche, Hang Zhao
1Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, USA. stefan.koenig@sepracor.com
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.
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