Process for 4-halomethyl-azetidinones by cyclization of O-acylhydroxamates

Patent

Description

A process for 4-halomethylazetidin-2-ones is provided which comprises mixing in an inert solvent a positive halogen reagent in the presence of a weak base with a .beta.,.gamma.-unsaturated O-acylhydroxamate of the formula ##STR1## wherein R is protected amino, lower alkyl or phenyl substituted lower alkyl, R.sub.2 is a substituent such as lower alkyl which may be substituted by formyl, hydroxy, halogen, etc., and R.sub.1 is alkoxy, benzyloxy, etc. When R is a protected amino group, the process provides cis-4-halomethylazetidin-2-ones, while when R is alkyl or phenylalkyl, the trans isomer is obtained. The 4-halomethylazetidinones are useful intermediates for known antibiotic compounds.

Attributes

Attribute NameValues
Title
  • Process for 4-halomethyl-azetidinones by cyclization of O-acylhydroxamates

Patent Number
  • US 4751296 B2

USPTO Link
Inventor
  • Marvin J. Miller

Inventor From Local Institution
  • Marvin J. Miller

Other Application
  • 06/893,748

Claims
  • 16

Classification (US Patent)
  • 540/355; 558/263;

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 205/08 (); C07D 403/04 (); C07D 413/04 (); C07B 039/00 ()

Language
  • eng

Date Issued
  • 1988-06-14

Publisher
  • United States Patent and Trademark Office

Assignee
  • University of Notre Dame Du Lac

Record Visibility Public
Content License
Departments and Units
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