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- Title
(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.
- Authors
Fu, Dong-Jun; Pham, Victor; Tippin, Matthew-Alexander; Song, Liankun; Zi, Xiaolin; Zhang, En; Liu, Hong-Min
- 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.
- Subjects
DIHYDROFURANS; DIAZABICYCLOHEPTENE; NUCLEAR magnetic resonance spectroscopy; CHEMICAL synthesis; LEWIS acids
- Publication
Molbank, 2018, Vol 2018, Issue 3, pm1016
- ISSN
1422-8599
- Publication type
Article
- DOI
10.3390/M1016