.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

1977-01-19

1978-09-12

Meyers, Albert T.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

42424851, 42424852, 42424853, 42424854, 42424855, 42424856, 42424857, 42424858, C07D26536, C07D49802, A01N 900, A01N 922

Patent

active

041139461

ABSTRACT:
There is described the stereoselective total synthesis by a variety of routes of novel suitably substituted .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 Q is hydrogen, alkyl, aralkyl or --CH.sub.2 COOZ where Z is hydrogen or the residue of an ester group and X is amino, azido or acylamino. Also included in the invention are compounds of the above formula 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. Those compounds in which X is acylamino and their physiologically hydrolyzed esters and pharmaceutically acceptable salts are potent antibacterial agents.

REFERENCES:
patent: 4011216 (1977-03-01), Menard et al.
patent: 4136648 (1977-03-01), Horning et al.
J. C. S. (Chem. Comm.), 1972, pp. 589-590, Brunwin & Towe.

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