Process for preparing Z and E-rotamers of 3-hydroxy cephem deriv

Details Process for preparing Z and E-rotamers of 3-hydroxy cephem deriv Process for preparing Z and E-rotamers of 3-hydroxy cephem deriv

1993-02-18

1995-04-25

Rizzo, Nicholas

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540221, C07D50104

Patent

active

054100445

ABSTRACT:
A process for the manufacture of 7-acylamino-3-hydroxycephem-4-carboxylate-1-oxide in E-rotamer form (Formula III), comprises reacting a 7-acylamino-3-exomethylenecepham-4-carboxylate-1-oxide with ozone in an inert organic solvent in the presence of a catalytic amount of an organic or inorganic base at a temperature ranging from about -80.degree. C. to about +20.degree. C. The E-rotamer (wherein the 3-hydroxy group is strongly hydrogen bonded to the carbonyl of the 4-ester group) exhibits different chemical and physical properties from and is more thermodynamically stable than, the Z-rotamer (wherein there is no hydrogen bonding between the 3-hydroxy group and the carbonyl of the 4-ester group).

REFERENCES:
patent: 3917587 (1975-11-01), Chauvette
patent: 4031084 (1977-06-01), Kukolja et al.
patent: 4389524 (1983-06-01), Scartazzini et al.
patent: 4477658 (1984-10-01), Scartazzini et al.
patent: 4591642 (1986-05-01), Scartazzini et al.
patent: 4668781 (1987-05-01), Scartazzini et al.

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