Preparation of 7-substituted amino-desacetoxycephalosporanic aci

Details Preparation of 7-substituted amino-desacetoxycephalosporanic aci Preparation of 7-substituted amino-desacetoxycephalosporanic aci

1975-05-05

1977-01-18

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602391, 260429R, 2604297, 2604488R, C07D50110

Patent

active

040038947

ABSTRACT:
Process for the preparation of 7-substituted amino-desacetoxycephalosporanic derivatives comprising converting a 6-substituted amino-penicillanic acid sulfoxide into an anhydride of a 6-substituted amino-penicillanic acid sulfoxide, heating the said acid anhydride intermediate at a temperature up to at most 160.degree. C in a dry inert organic solvent with an anhydrous acid which is capable of causing ring expansion of the penam ring to a .DELTA..sup.3 -cephem ring, in the presence of a silicon-containing compound capable of (a) removing water formed during the ring enlargement of the penam structure fast enough to prevent water hydrolysis of the acid anhydride moiety present and (b) forming neutral or basic products on hydrolysis, the aforesaid acid being strong enough not to be, or not to a substantial extent to be, silylated under the reaction conditions employed, and hydrolyzing the resulting compound in situ to form the .DELTA..sup.3 -7-substituted amino-desacetoxycephalosporanic acid as such or as a salt, such as alkali metal, alkaline earth metal or amine salt and to the novel sulfoxide acid anhydrides formed therein.

REFERENCES:
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patent: 3573295 (1971-03-01), Johnson et al.
patent: 3632850 (1972-07-01), Garbrecht
patent: 3637678 (1973-01-01), Webber et al.
patent: 3668202 (1972-06-01), Foster et al.
patent: 3671449 (1972-06-01), Jackson
patent: 3674775 (1972-07-01), Spry
patent: 3725397 (1973-04-01), Graham et al.
patent: 3725399 (1973-04-01), Ellerton et al.
Cotton et al., "Advanced Inorganic Chemistry," 1966, p. 465 (Interscience publishers).

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