Process for the preparation of 7-acylamino-3-hydroxycephem-4-carboxylic acids and 7-acylamino-3-hydroxy-1-dethia-1-oxacephem-4-carboxylic acids

• Main Authors: HARTWIG,WOLFGANG,.DR, HAEBICH,DIETER,.DR
• Format: Patent
• Language: English; German
• Published: 28.11.1985
• Edition: 4
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

The invention relates to a process for the preparation of 7-acylamino-3-hydroxycephem-4-carboxylic acids and 7-acylamino-3-hydroxy-1-dethia-1-oxacephem-4-carboxylic acids and their derivatives of the general formula (I) in which R , R and X have the meaning given in the description, by reaction of compounds of the general formula (4) with a compound of the formula (5) in which R and X have the meaning given and Y represents diazo (N2) or hydrogen (H2), in an inert solvent in the presence of a Lewis acid or protonic acid catalyst. According to one variant of the process, compounds of the formula (4) are reacted with a compound of the formula (6> HX-CH2-C IDENTICAL C-COOR as described above, the triple bond of the intermediate compound formed in this reaction is hydrated and the compounds of the general formula (3) thus obtained for Y = hydrogen (for Y = diazo the compounds of the general formula (2) result directly) are reacted in a solvent with an azide and the compound of the formula (2) is irradiated or heated in the presence of a catalyst so that the compounds of the general formula (1) result.