Amino acid derivatives, their production and use in preparing ca

Details Amino acid derivatives, their production and use in preparing ca Amino acid derivatives, their production and use in preparing ca

1991-02-27

1992-06-02

Shippen, Michael L.

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

Organic compounds

Carboxylic acid esters

560 24, 560 29, 560 33, 560157, 560160, 560163, C07C26100

Patent

active

051188317

ABSTRACT:
Novel amino acid derivatives of the formula ##STR1## wherein R.sup.1 is a protecting group removable under reducing or acid conditions, and R.sup.2 and R.sup.5 are hydrogen or carboxylic protecting groups, are useful as intermediates in preparing stereospecific carbapenam/carbapenem derivatives. R.sup.1 is removed under reducing conditions to form a pyrrolidine derivative, which is further cyclized from the R.sup.5 .dbd.H compound to form a .beta.-lactam ring. Stereospecificity at the 6-position is achieved by treatment with lithium diisopropylamide (LDA) and quenching at different temperatures. Compound (I) can be prepared by treating R.sup.1 -protected R.sup.3 -pyrrolidone carboxylic acid R.sup.2 -ester with a lithium enolate of the formula R.sup.4 CHLiCO.sub.2 R.sup.5. The lithium enolate can be formed from R.sup.4 CH.sub.2 CO.sub.2 R.sup.5 by treatment with LDA.

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