Process for intermediates to 1-carbapenems and 1-carbacephems

Details Process for intermediates to 1-carbapenems and 1-carbacephems Process for intermediates to 1-carbapenems and 1-carbacephems

C - Chemistry, Metallurgy

07

D

260/310.1, 260/3

C07D 417/06 (2006.01) C07D 417/14 (2006.01) C07F 5/04 (2006.01)

Patent

CA 1332417

ABSTRACT A stereoselective process for chiral intermediates to 1-carbapenum and 1-carbacephalosporin antibiotics 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. Benzyl 3,3-(ethylenedioxy)-4- formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thia- zolidine-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.

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