US4595532.pdf (1.67 MB)
N-(substituted-methyl)-azetidin-2-ones
N-Mono or N-disubstituted methyl-2-azetidinones are provided via cyclization of .beta.-hydroxy or .beta.-halo substituted acid sec-amides wherein the amide nitrogen is substituted with a mono- or di-substituted methyl group having activating substituents. Cyclization of .beta.-hydroxy acid amides is mediated by triphenylphosphine-dialkylazodicarboxylate while cyclization of .beta.-halo acid amides is mediated by strong bases e.g. lithium dialkylamides. E.g. Diethyl amino-protected L-serylaminomalonate is cyclized with 200 mole % TPP-diisopropylazodicarboxylate to N-(diethoxycarbonylmethyl)-3-protected-amino-2-azetidinone. The 2-azetidinones provided are useful intermediates.
History
Patent Number
US 4595532 B2Other Application
06/718,127Inventor
Marvin J. MillerInventor from Local Institution
Marvin J. MillerAssignee
University of Notre Dame Du LacDate Modified
2016-06-07Language
- English
Claims
18Publisher
United States Patent and Trademark OfficeCooperative Patent Classification Codes
C07D 205/08 (20130101); C07D 205/085 (20130101); C07D 413/04 (20130101); C07D 403/04 (20130101); C07D 207/277 (20130101)Contributor
Marvin J. MillerInternational Patent Classification Codes
C07D 205/00 (20060101); C07D 205/08 (20060101); C07D 207/00 (20060101); C07D 205/085 (20060101); C07D 207/277 (20060101); C07D 403/04 (20060101); C07D 413/00 (20060101); C07D 413/04 (20060101); C07D 403/00 (20060101); C07D 205/08 (); C07D 413/04 (); C07D 403/04 (); C07D 401/12 ()US Patent Classification Codes
540/363; 540/200; 540/360; 540/364; 548/231;Usage metrics
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