Document Type
Article
Publication Date
3-19-2020
Publication Title
Tetrahedron Letters
Volume
61
Issue
12
Pages
151632
Publisher Name
Elsevier
Abstract
The hydrochloride salt of ɑ-aminocyclobutanone protected as its dimethyl acetal 2,2-dimethoxycyclobutan-1-aminium chloride (3) has been prepared as a modular synthon for convenient access to cyclobutanone-containing lead inhibitors of hydrolase enzymes including serine proteases and metalloproteases. Protected ɑ-aminocyclobutanone 3 was converted to representative amide and sulfonamide-functionalized 2-aminocyclobutanone derivatives. Reaction of the amino acetal 3 with phenyl isothiocyanate afforded the bicyclic urea 1-hydroxyl-2,4-diazabicyclo[3.2.0]heptane-3-thione (9) as confirmed by a single crystal X-ray structure.
Recommended Citation
Habeeb Mohammad, Thahani S.; Reidl, Cory T.; Zeller, Matthias; and Becker, Daniel P. Ph.D.. Synthesis of a Protected 2-Aminocyclobutanone as a Modular Transition State Synthon for Medicinal Chemistry. Tetrahedron Letters, 61, 12: 151632, 2020. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1016/j.tetlet.2020.151632
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
Copyright Statement
© Elsevier Ltd, 2020.
Comments
Author Posting © Elsevier Ltd, 2020. This is the author's version of the work. It is posted here by permission of Elsevier Ltd for personal use, not for redistribution. The definitive version was published in Tetrahedron Letters, Volume 61, Issue 12, March 2020. https://doi.org/10.1016/j.tetlet.2020.151632