Process for preparing di-7-azido cephalosporin compounds

Details Process for preparing di-7-azido cephalosporin compounds Process for preparing di-7-azido cephalosporin compounds

1976-03-30

1978-07-04

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

424246, 2603067C, 544 53, 544 30, C07D50104

Patent

active

040990001

ABSTRACT:
A novel total synthesis process is provided, yielding cephalosporin or penicillin compounds. The process uses as starting material a glycine ester, which first is reacted to yield a dihydrothiazine, and subsequently condensed with azidoacetyl chloride to form the cepham nucleus, then dehydrated to yield the desired 3-unsaturation. Subsequent reduction and acylation steps are analogous to known chemistry. The end products are antibacterial agents.

REFERENCES:
Vanderhaeghen et al., J. Med. Chem. vol. 18, 486-489 (1975).
Bose et al., JACS 4506-4508 (1968).
Guthikonda et al., JACS 7584-7585 (1974).
Cama et al.,JACS 7582-7584 (1974).
Firestone et al., J. Org. Chem. vol. 39, pp. 3384-3387, 437-440 (1974).
Steinberg et al., Tetrahedron Letters pp. 3567-3570 (1974).
Ratcliffe et al., Tetrahedron Letters pp. 4653-4656 4649-4652, 4652, 4645-4648 (1973).

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