115500-88-4Relevant articles and documents
Amino acid derivatives, their production and use in preparing carbapenem and carbapenam compounds
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, (2008/06/13)
Novel amino acid derivatives of the formula STR1 wherein R1 is a protecting group removable under reducing or acid conditions, and R2 and R5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R5 =H compound to form a β-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different termperatures. Compound (I) can be prepared by treating R1 -protected R3 -pyrrolidone carboxylic acid R2 -ester with a lithium enolate of the formula R4 CHLiCO2 R5. The lithium enolate can be formed from R4 CH2 CO2 R5 by treatment with LDA.