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Molbank 2018, 2018(3), M1016; https://doi.org/10.3390/M1016

(1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one

1
School of Pharmaceutical Sciences & Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou University, Zhengzhou 450001, China
2
Department of Urology, University of California, Irvine, Orange, CA 92868, USA
*
Author to whom correspondence should be addressed.
Received: 11 August 2018 / Revised: 25 August 2018 / Accepted: 28 August 2018 / Published: 30 August 2018
(This article belongs to the Special Issue Molecules from Catalytic Processes)
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Abstract

Efficient large-scale and feasible industrial synthesis of the 1-oxacephem core structure from 6-aminopenicillanic acid (6-APA) has been reported for several decades. Via the industrial synthesis route, a byproduct (compound 9) containing a butenolide unit was purified and characterized by NMR and HRMS in this work. It is worth noting that compound 9 is an entirely new compound. Additionally, a plausible mechanism and effects on the formation of 9 by different Lewis acids were proposed. The discovery of compound 9 could improve the purity of this feasible industrial synthesis and provide considerable cost savings. View Full-Text
Keywords: industrial feasible synthesis; 6-APA; butenolide; 1-oxacephem industrial feasible synthesis; 6-APA; butenolide; 1-oxacephem
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Fu, D.-J.; Pham, V.; Tippin, M.-A.; Song, L.; Zi, X.; Zhang, E.; Liu, H.-M. (1R,5S)-6-(4-Methyl-2-oxo-2,5-dihydrofuran-3-yl)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one. Molbank 2018, 2018, M1016.

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