Process for the preparation of 3-substituted-2-azetidinones

Patent

Description

Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; wherein R.sub.1 is said nucleophile; R is hydrogen, or protected amino, R.sub.2 is R.sub.4 as defined herein below; R.sub.3 is a leaving group; and R.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a group of the formula wherein R.sub.6 is 2-furyl, naphthyl, phenyl, phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; or R.sub.6 is a group of the formula in which R.sub.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, phenyl, or benzyl or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; or R.sub.4 is a group of the formula ##STR3## wherein L is –OR.sub.7 where R.sub.7 is as defined; or R.sub.4 is a group of the formula ##STR4## wherein: G is trimethylsilylmethyl, hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 substituted alkyl, phenyl, or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido.

Attributes

Attribute NameValues
Title
  • Process for the preparation of 3-substituted-2-azetidinones

Patent Number
  • US 5250676 B2

USPTO Link
Inventor
  • Catherine M. Gasparski

  • Marvin J. Miller

  • Min Teng

Inventor From Local Institution
  • Marvin J. Miller

Other Application
  • 07/855,402

Claims
  • 6

Classification (US Patent)
  • 540/200; 540/205; 540/355; 540/360; 540/362; 540/363; 540/364;

Cooperative Patent Classification codes
  • C07D 205/08 (20130101); C07D 463/00 (20130101); C07D 403/04 (20130101); C07D 205/085 (20130101)

International Patent Classification codes
  • C07D 205/085 (20060101); C07D 205/00 (20060101); C07D 205/08 (20060101); C07D 403/04 (20060101); C07D 403/00 (20060101); C07D 463/00 (20060101); C07D 205/85 (); C07D

Language
  • eng

Date Issued
  • 1993-10-05

Publisher
  • United States Patent and Trademark Office

Assignee
  • University of Notre Dame Du Lac

Record Visibility and Access Public
Content License
Departments and Units
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Collections Featuring this Patent
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