Display options
Cite
Koenig SG, Vandenbossche CP, Zhao H, et al. A facile deprotection of secondary acetamides. Org Lett. 2009;11(2):433-6doi: 10.1021/ol802482d.
Koenig, S. G., Vandenbossche, C. P., Zhao, H., Mousaw, P., Singh, S. P., & Bakale, R. P. (2009). A facile deprotection of secondary acetamides. Organic letters, 11(2), 433-6. https://doi.org/10.1021/ol802482d
Koenig, Stefan G, et al. "A facile deprotection of secondary acetamides." Organic letters vol. 11,2 (2009): 433-6. doi: https://doi.org/10.1021/ol802482d
Koenig SG, Vandenbossche CP, Zhao H, Mousaw P, Singh SP, Bakale RP. A facile deprotection of secondary acetamides. Org Lett. 2009 Jan 15;11(2):433-6. doi: 10.1021/ol802482d. PMID: 19128192.
Copy Download .nbib Format: NLM
Share it on

Org Lett. 2009 Jan 15;11(2):433-6. doi: 10.1021/ol802482d.

A facile deprotection of secondary acetamides.

Organic letters

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

Affiliations

  1. Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, Massachusetts 01752, USA. [email protected]

PMID: 19128192 DOI: 10.1021/ol802482d

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.

Publication Types