Process for intermediates to 1-carbapenems and 1-carbacephems

Patent

Description

A stereoselective process for chiral intermediates to 1-carbapenem and 1-carbacephalosporins is provided comprising the use of an N-acyl-(4R)-substituted-1,3-thiazolidine-2-thione as a chiral auxiliary in boron enolate mediated aldol condensation with a protected-.beta.-keto ester aldehyde. E.g., benzyl 3,3-(ethylenedioxy)-4-formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thiazolidine-2-thione to provide benzyl 3,3-ethylenedioxy-(5R)-hydroxy-6-[(4R)-methoxycarbonyl-1,3-thiazolidine-2- thione-3-ylcarbonyl]octanoate. Displacement of the thiazolidine-2-thione chiral auxiliary moiety with an O-alkyl, O-acyl or O-aralkyl hydroxyamine provides the corresponding chiral intermediate as the hydroxamate.

Attributes

Attribute NameValues
Title
  • Process for intermediates to 1-carbapenems and 1-carbacephems

Patent Number
  • US 4845229 B2

USPTO Link
Inventor
  • Chi-Nung W. Hsiao

  • Marvin J. Miller

Inventor From Local Institution
  • Marvin J. Miller

Other Application
  • 07/160,801

Claims
  • 5

Classification (US Patent)
  • 548/110;

Cooperative Patent Classification codes
  • C07D 317/30 (20130101); C07F 5/025 (20130101); C07D 417/06 (20130101)

International Patent Classification codes
  • C07D 317/30 (20060101); C07D 317/00 (20060101); C07D 417/00 (20060101); C07F 5/02 (20060101); C07F 5/00 (20060101); C07D 417/06 (20060101); C07D 277/06 ()

Language
  • eng

Date Issued
  • 1989-07-04

Publisher
  • United States Patent and Trademark Office

Assignee
  • University of Notre Dame Du Lac

Record Visibility and Access Public
Content License
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