Process and intermediates for .beta.-lactam antibiotics
AssigneeHarvard University
InventorsDavid A. Evans, Eric B. Sjogren
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Abstract
1-Benzyl (or substituted benzyl)-3.beta.-[4(S)-aryloxazolidin-2-one-3-yl]-4.beta.-(2-arylvinyl)azet idin-2-ones are provided via cycloaddition of a 4(S)-aryloxazolidin-2-one-3-ylacetyl halide and an imine formed with a benzylamine and a 3-arylacrolein, e.g. cinnamaldehyde. The azetidinones are useful chiral intermediates in an asymmetric synthesis of 1-carba(1-dethia)-3-hydroxy-3-cephem-4-carboxylic acids and esters and to monocyclic .beta.-lactam antibiotics.
Claims11
A compound of the formula ##STR26## wherein Ar is phenyl, C.sub.1 -C.sub.4 alkylphenyl, halophenyl, C.sub.1 -C.sub.4 alkoxyphenyl, naphthyl, thienyl, furyl, benzothienyl, or benzofuryl;
- R is phenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, or halophenyl;
- Y is --CH.dbd.CH--, or --CH.sub.2 --CH.sub.2 --;
- and R' is phenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, halophenyl, furyl or naphthyl.
The compound of the formula ##STR27## wherein Ar is phenyl, C.sub.1 -C.sub.4 alkylphenyl, halophenyl, C.sub.1 -C.sub.4 alkoxyphenyl, napthyl, thienyl, furyl, benzothienyl, or benzofuryl;
- R is phenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, or halophenyl;
- and R.sub.4 is formyl, carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl, methyl, halomethyl or hydroxymethyl, and when R.sub.4 is other than formyl the 4-position epimers thereof.
Dependencies are inferred from the claim text.