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(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.
Molbank 2018, 2018(3), M1016; https://doi.org/10.3390/M1016
Received: 11 August 2018 / Revised: 25 August 2018 / Accepted: 28 August 2018 / Published: 30 August 2018
(This article belongs to the Collection Molecules from Catalytic Processes)
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
MDPI and ACS Style

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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