Process for producing 7-amino-7-alkoxycephalosporins

Details Process for producing 7-amino-7-alkoxycephalosporins Process for producing 7-amino-7-alkoxycephalosporins

1979-04-13

1980-12-30

Rizzo, Nicholas S.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

424246, C07D50118

Patent

active

042425093

ABSTRACT:
A 7-(5-amino-5-carboxyvaleramido)-7-methoxycephalosporin with amino and acid groups protected is reacted with PCl.sub.5 or other agent capable of forming an imino halide; the resulting imino halide is thereafter reacted under essentially non-aqueous conditions with a primary loweralkanol of C.sub.1 -C.sub.4 or with methan-d.sub.3 -ol, yielding nucleus bearing a 7-alkoxy group derived from the primary loweralkanol or methan-d.sub.3 -ol. In situ acylation of the nucleus affords 7-acylamido-7-alkoxycephalosporins in good yield; these products can be deesterified to yield the corresponding acids, which exhibit antibacterial activity.

REFERENCES:
patent: 3780034 (1973-12-01), Christensen et al.
patent: 3897424 (1975-07-01), Koppel et al.
patent: 3920638 (1975-11-01), Bickel et al.
patent: 4031086 (1977-06-01), Karady et al.
patent: 4103083 (1978-07-01), Ogawa et al.
C. A., vol. 71, col. 61403wc, 1969.
Karady et al., Tetrahedron Letters, No. 28, pp. 2401-2404, (1976).
Morrison et al., Organic Chemistry, pp. 741-742, (1966), 2nd Edition.

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