Process for preparing cephalosporanic acid compounds

Details Process for preparing cephalosporanic acid compounds Process for preparing cephalosporanic acid compounds

1980-10-03

1982-11-09

Rizzo, Nicholas S.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 26, 2602391, 424246, C07D50106

Patent

active

043585884

ABSTRACT:
A process for the preparation of [D-.alpha.-amino-p-hydroxyphenylacetamido]-penicillanic acid or cephalosporanic acid compounds comprising reacting a compound having a formula selected from the group consisting of ##STR1## wherein X is selected from the group consisting of hydrogen, acetoxy and five-membered heterocyclic group containing at least one hetero atom of the group consisting of oxygen, sulfur and nitrogen and optionally substituted with e.g. lower alkyl, this residue being attached to the 3-CH.sub.2 group via sulfur atom and wherein a NH radical if present has optionally been silylated with at least one mole equivalent of a silylating agent producing ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of lower alkyl, benzyl, cycloalkyl and phenyl in an inert anhydrous, organic solvent, preferably a water-inmiscible organic main-solvent, to form a compound having a formula selected from the group consisting of ##STR3## adjusting the pH to a scale value of 5.5 to 7.5 and reacting the resulting compounds in a pre-cooled solution with an at least equimolar amount of a compound of the formula wherein R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.6 and R.sub.7 are lower alkoxy.

REFERENCES:
patent: 3965098 (1976-06-01), Robinson
patent: 4148817 (1979-04-01), Wright

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