Process for preparing 7.beta.-acylamino-7.alpha.-alkoxycephalosp

Details Process for preparing 7.beta.-acylamino-7.alpha.-alkoxycephalosp Process for preparing 7.beta.-acylamino-7.alpha.-alkoxycephalosp

1975-03-04

1976-06-01

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260243C, 424246, 424271, C07D49944, C07D50120

Patent

active

039608450

ABSTRACT:
A process for preparing a 7.beta.-acylamino-7.alpha.alkoxycephalosporin or 6.beta.-acylamino-6.alpha.-alkoxypenicillin which comprises either (a) reacting a 7.beta.-(.alpha.'-halogeno or .alpha.'-hydroxyacylamino)cephalosporin or 6.beta.-(.alpha.'halogeno or .alpha.'-hydroxyacylamino)penicillin with a halogenating agent to give a .alpha.-halogeno-iminohalide, reacting the latter compound with an equimolar amount of an alkali metal alkoxide in the presence of one equivalent amount of a base to give a 7.alpha.-alkoxyketeneimine and subjecting the latter compound to hydration; or (b) reacting the 7.beta.-(.alpha.'-halogeno or .alpha.'hydroxyacylamino)cephalosporin or 6.beta.-(.alpha.'-halogeno or .alpha.'-hydroxyacylamino) penicillin with the halogenating agent to give the .alpha.-halogeno-iminohalide, reacting the latter compound with two equimolar amounts of the alkali metal alkoxide in the presence of one equivalent amount of the base to give a dialkoxyimino compound, reacting the latter compound with a halogeno-silyl compound or an acid and treating the resulting product with water.
The final products are useful as antibacterial agents or intermediates thereof.

REFERENCES:
patent: 3778432 (1973-12-01), Pines
patent: 3843641 (1974-10-01), Christensen et al.
Firestone et al, J. Org. Chem. 38 1436 (1973).
Koppel et al., J. Amer. Chem. Soc. 95 2403 (1973).

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