PRODUCTION OF THIOVINYL CEPHALOSPORIN DERIVATIVE

• Main Authors: MASUYA HIRONAGA, MATSUMOTO NORICHIKA
• Format: Patent
• Language: English
• Published: 23.02.1999
• Edition: 6
• Subjects: APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS; THEIR RELEVANT APPARATUS; TRANSPORTING

PROBLEM TO BE SOLVED: To obtain the subject compound as E-form in high yield through few processes capable of producing cephalosporin derivatives having antibacterial action in an industrially advantageous way, by reaction of a specific compound with a disulfide compound in the presence of a phosphorus compound. SOLUTION: This compound of formula II (R is a group interposed with a sulfur atom) is obtained by reaction of a compound of formula I (R is a protected or acrylated amino; R is carboxyl) or a salt thereof with a disulfide compound in the presence of a phosphorus compound (pref. a trivalent phosphorus compound such as tri-n-butylphosphine), wherein the disulfide compound is e.g. a compound of the formula r -S-S-R (R is a hydrocarbon or heterocycle) such as 4-pyridyl sulfide. The amounts of the disulfide compound and the phosphorus compound to be used are pref. 1.5-2 equivalents and 1.1-1.2 equivalents per mol of the compound (salt) of formula I, respectively; and the above reaction is normally carried out in a solvent (pref. N-methylpyrrolidone).