Process for the stereospecific synthesis of azetidinones

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

1994-06-23

1996-10-01

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540360, 540362, 540363, 540364, C07D20508, C07D20509, C07B 4306

Patent

active

055612270

ABSTRACT:
This invention provides an improved process for producing azetidinones. More particularly, this invention provides the steps of producing an azetidinone represented by the formula I ##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: (a) converting a carboxylic acid to the corresponding acid chloride; (b) deprotonating a chiral oxazolidinone and treating the resulting anion with the product of step (a); (c) enolizing the product of step (b) and condensing with an imine; and (d) cyclizing the product of step (c). Steps (c) and (d) of this process are as shown in the following reaction scheme. ##STR2##

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