Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1983-03-28
1986-01-21
Berch, Mark L.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
2602454, 2603303, 2603309, C07D41112
Patent
active
045656541
ABSTRACT:
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.
REFERENCES:
patent: 4337197 (1982-06-01), Gordon
patent: 4386034 (1983-05-01), Floyd et al.
Miller et al., J. Amer. Chem. Soc. 102, 7030 (1980).
Mattingly et al., Chem. Abs. 94, 197018x (1981).
Miller et al. II, Tetrahedron 39, 2571-75 (1983).
D. M. Floyd et al., "Monobactams. Preparation of (S)-3-Amino-2-Oxoazetidine-1-Sulfonic Acids from L-.alpha.-Amino-.beta.-Hydroxy Acids via Their Hydroxamic Esters", J. Org. Chem. 1982, 47, 5160-5167.
D. M. Floyd et al., "Monobactams. Stereospecific Synthesis of (S)-3-Amino-2-Oxoazetidine-1-Sulfonic Acids", J. Org. Chem., 1982, 47, 176-178.
Berch Mark L.
Scanlon William B.
University of Notre Dame du Lac
Whale Arthur R.
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