.DELTA..sup.2,3 -1,4-Morpholine-2-carboxylic acid derivatives as

Details .DELTA..sup.2,3 -1,4-Morpholine-2-carboxylic acid derivatives as .DELTA..sup.2,3 -1,4-Morpholine-2-carboxylic acid derivatives as

1977-01-27

1978-10-03

Meyers, Albert T.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

42424851, 42424852, C07D26536, C07D49802, A01N 900, A01N 922

Patent

active

041185668

ABSTRACT:
There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein X is amino, azido or acylamido and Z represents optionally substituted C.sub.1 -C.sub.6 alkyl, aryl, aralkyl or heterocyclic. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.

REFERENCES:
patent: 4011216 (1977-03-01), Menard et al.
patent: 4012383 (1977-03-01), Belleau et al.
J. C. S. (Chem. Comm.), 1972, pp. 589-590, Brunwin & Lowe.

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