N-(substituted-methyl)-azetidin-2-ones

Patent

Description

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.

Attributes

Attribute NameValues
Title
  • N-(substituted-methyl)-azetidin-2-ones

Patent Number
  • US 4595532 B2

USPTO Link
Inventor
  • Marvin J. Miller

Inventor From Local Institution
  • Marvin J. Miller

Other Application
  • 06/718,127

Claims
  • 18

Classification (US Patent)
  • 540/363; 540/200; 540/360; 540/364; 548/231;

Cooperative Patent Classification codes
  • C07D 205/08 (20130101); C07D 205/085 (20130101); C07D 413/04 (20130101); C07D 403/04 (20130101); C07D 207/277 (20130101)

International 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 ()

Language
  • eng

Date Issued
  • 1986-06-17

Publisher
  • United States Patent and Trademark Office

Assignee
  • University of Notre Dame Du Lac

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