Process for the stereospecific synthesis of azetidinones

Details Process for the stereospecific synthesis of azetidinones Process for the stereospecific synthesis of azetidinones

1992-10-19

1994-04-26

Berch, Mark L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540362, C07D20508, C07B 5300

Patent

active

053068173

ABSTRACT:
This invention provides an improved process for producing azetidinones. More particularly, this invention provides the steps of producing an trans-azetidinone represented by the formula ##STR1## from a carboxylic acid R.sup.2 -D-CH.sub.2 -COOH, an aldehyde R.sup.1 -A-CHO and an amine RNH.sub.2, by the steps of: (a1) converting a carboxylic acid to the corresponding acid chloride; (b1) deprotonating a chiral oxazolidinone and treating the resulting anion with the product of step (a1); (c1) enolizing the product of step (b1) and condensing with the aldehyde; (d1) hydrolyzing the product of step (c1); (e1) condensing the product of step (d1) with the amine; and (f1) cyclizing the product of step (e1).
Alternatively, the process comprises (a2) enolizing the product of step (b1) and condensing, in the presence of a Lewis acid, with a Schiff's base prepared from the aldehyde and the amine; and (b2) cyclizing the product of step (a2).

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