Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1974-08-05
1984-06-26
Daus, Donald G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544 22, 544 24, 544 25, 544 26, 544 27, 544 28, 544 29, 544 30, 424246, C07D50100, A61K 31545
Patent
active
044567553
ABSTRACT:
In accordance with this invention, it has been found that the oxygen analog of 7-aminocephalosporanic acid and biologically active derivatives thereof can be formed from esters of 7-aminocephalosporanic acid. Esters of 7-oxocephalosporanic acid can be formed by diazotization of an ester of 7-aminocephalosporanic acid and contact of the diazo compound so formed with a hypohalous acid and a base in a water miscible organic solvent. Oxygen analogs of 7-aminocephalosporins isolated as esters are then formed by reducing the aforesaid ester to the corresponding 7.beta.-hydroxy-cephalosporanate and then forming the desired analog by introduction of a side chain via hydroxyl group modification. Oxygen analogs of 7-aminocephalosporins are then formed by regeneration of the acid via protective group removal.
REFERENCES:
patent: 3976641 (1976-08-01), Hoover et al.
patent: 4020057 (1977-04-01), Gleason
Sheehan et al., J. Org. Chem., vol. 39, No. 10, pp. 1444-1445, May 17, 1974.
Lo Young S.
Sheehan John C.
Conlin David G.
Daus Donald G.
Massachusetts Institute of Technology
Neuner George W.
Rivers Diana G.
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