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

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posted on 2016-06-07, 00:00 authored by Marvin J MillerMarvin J Miller
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 B2

Other Application

06/718,127

Inventor

Marvin J. Miller

Inventor from Local Institution

Marvin J. Miller

Assignee

University of Notre Dame Du Lac

Date Modified

2016-06-07

Language

  • English

Claims

18

Publisher

United States Patent and Trademark Office

Cooperative 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. Miller

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 ()

US Patent Classification Codes

540/363; 540/200; 540/360; 540/364; 548/231;

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