N-Acyloxy monocyclic .beta.-lactams

Patent

Description

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.

Attributes

Attribute NameValues
Title
  • N-Acyloxy monocyclic .beta.-lactams

Patent Number
  • US 4565654 B2

USPTO Link
Inventor
  • Marvin J. Miller

Inventor From Local Institution
  • Marvin J. Miller

Other Application
  • 06/479,375

Claims
  • 12

Classification (US Patent)
  • 540/355; 548/229; 548/237; 548/239;

Cooperative Patent Classification codes
  • C07D 205/085 (20130101); C07D 205/08 (20130101)

International Patent Classification codes
  • C07D 205/08 (20060101); C07D 205/00 (20060101); C07D 205/085 (20060101); C07D 411/12 ()

Language
  • eng

Date Issued
  • 1986-01-21

Publisher
  • United States Patent and Trademark Office

Assignee
  • University of Notre Dame Du Lac

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