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Process for intermediates to 1-carbapenems and 1-carbacephems
A stereoselective process for chiral intermediates to 1-carbapenum and 1-carbacephalosporins 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. E.g., benzyl 3,3-(ethylenedioxy)-4-formylbutyrate is condensed with the boron enolate formed with n-butyryl (4R)-methoxycarbonyl-1,3-thiazolidine-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.
History
Patent Number
US 4745201 B2Other Application
06/780,101Inventor
Chi-Nung W. Hsiao Marvin J. MillerInventor from Local Institution
Marvin J. MillerAssignee
University of Notre Dame Du LacDate Modified
2016-06-07Language
- English
Claims
9Publisher
United States Patent and Trademark OfficeCooperative Patent Classification Codes
C07D 317/30 (20130101); C07F 5/025 (20130101); C07D 417/06 (20130101)Contributor
Marvin J. MillerInternational Patent Classification Codes
C07D 317/00 (20060101); C07D 317/30 (20060101); C07F 5/00 (20060101); C07D 417/00 (20060101); C07F 5/02 (20060101); C07D 417/06 (20060101); C07D 317/26 ()US Patent Classification Codes
549/452; 548/110; 548/188;Usage metrics
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