Process for the preparation of 7-amino-3-((Z)-1-propen-1yl)-3-cephem-4-carboxylic acid

US5132419A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Joachim Lanz · Wuppertal, DE
• Paul Naab · Bad Reichenhall, DE
• Ulrich Rosentreter · Binnen, DE

Key dates

• Filing date: Sep 27, 1990
• Grant date: Jul 21, 1992
• Expiry date: Sep 27, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D501/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

(7-APCA) having the formula (I) ##STR1## which is an important synthesis intermediate in the preparation of cephalosporin-like antibiotics, is prepared by treating a compound of the formula (II) ##STR2## in which R.sub.1 and R.sub.2 represent alkyl, aryl and aralkyl radicals, with a strong protonic acid or with a Lewis acid. Compound (II) is prepared by adding triphenylphosphine and alkali metal iodide to a compound of the formula (VI) ##STR3## then reacting with acetaldehyde in base. Compound (VI) is prepared by treating a compound of the formula (VII) ##STR4## with a base in a polar solvent at -70.degree. C. to 0.degree. C. Compound (VII) is prepared by treating a compound of the formula (VIII) ##STR5## with a chlorinating agent in an organic solvent.