Process for the production of a 7-methoxycephalosporine derivati

Details Process for the production of a 7-methoxycephalosporine derivati Process for the production of a 7-methoxycephalosporine derivati

1980-08-15

1982-04-13

Rizzo, Nicholas S.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

424246, C07D50104

Patent

active

043248918

ABSTRACT:
A new, efficient process is provided for the production of 7.beta.-[(2D-2-amino-2-carboxy)-ethylthio-acetamido]-7.alpha.-methoxy-3-[( 1-methyl-1H-tetrazole-5-yl) thiomethyl]-3-cephem-4-carboxylic acid useful as new antibacterial agent. This process is economic in using as the starting material the inexpensive, corresponding cephem compound containing no 7.alpha.-methoxy group on the cephem nucleus and comprises 7.alpha.-methoxylation of a protected derivative of the starting cephem compound with t-butyl hypochlorite and lithium methoxide, followed by inactivation of the excessive methoxylation reagents with a trialkyl phosphite and acetic acid to prevent undesired side-reactions such as oxidation of the alkylthioacetyl group of the product, and further by conventional removal of the protecting groups.

REFERENCES:
patent: 4051320 (1973-09-01), Yanagisawa et al.
patent: 4202973 (1980-05-01), Taylor et al.
patent: 4229573 (1980-10-01), Shibuya et al.

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