US4675399.pdf (1.3 MB)
Cyclization process for .beta.-lactams
Process for N-acyloxy or sulfooxy 2-azetidinones comprising O-acylation of a .beta.-hydroxy or .beta.-halo hydroxamic acid, and cyclizing the O-acylhydroxamate with TPP-CCl.sub.4 -TEA or with TPP-dialkylazodicarboxylate to the N-acyloxy-2-azetidinone. Solvolysis of the acyl group provides an N-hydroxy-2-azetidinone. e.g., N-Cbz-L-serine is converted to the O-acetyl hydroxamate, cyclized and solvolyzed to N-hydroxy-3-(Cbz-amino)-2-azetidinone. The N-hydroxy-2-azetidinones are useful intermediates to monocyclic .beta.-lactam antibiotics and .beta.-lactamase inhibitors.
History
Patent Number
US 4675399 B2Other Application
06/783,705Inventor
Marvin J. MillerInventor from Local Institution
Marvin J. MillerAssignee
University of Notre Dame Du LacDate Modified
2016-06-07Language
- English
Claims
15Publisher
United States Patent and Trademark OfficeCooperative Patent Classification Codes
C07D 205/085 (20130101); C07D 205/08 (20130101)Contributor
Marvin J. MillerInternational Patent Classification Codes
C07D 205/00 (20060101); C07D 205/08 (20060101); C07D 205/085 (20060101); C07D 411/12 ()US Patent Classification Codes
540/355;Usage metrics
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