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Published August 12, 2013 | Supplemental Material + Published
Journal Article Open

A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand


An efficient method for the synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyOx) ligand has been developed. Inconsistent yields and tedious purification in known routes to (S)-t-BuPyOx suggested the need for an efficient, dependable, and scalable synthetic route. Furthermore, a route suitable for the synthesis of PyOx derivatives is desirable. Herein, we describe the development of a three-step route from inexpensive and commercially available picolinic acid. This short procedure is amenable to multi-gram scale synthesis and provides the target ligand in 64% overall yield.

Additional Information

© 2013 Shimizu et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Received: 06 June 2013; Accepted: 15 July 2013; Published: 12 August 2013. This publication is based on work supported by NIH-NIGMS (R01GM080269-01), and the authors additionally thank Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. J.C.H. thanks the American Chemical Society Division of Organic Chemistry for a graduate research fellowship. We also thank Shionogi & Co., Ltd. for a research grant and fellowship to H.S.

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Published - 1860-5397-9-187.pdf

Supplemental Material - 1860-5397-9-187-S1.pdf


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