Process for converting penicillin sulfoxides to the corresponding 3-desacetoxycephalosporins
AssigneeNovo Industri A/S
InventorsPoul Borrevang, Henning Borge Petersen
Life of this patent
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Abstract
Conversion of penicillin sulfoxides to the corresponding 3-desacetoxycelphalosporins are carried out in high yield by heating, e.g. 80.degree.-130.degree. C, a solvent solution of the penicillin in the presence of a complex formed by a phosphite or phosphine amide with the salt of a strong acid and a nitrogenous base, e.g. alpha-picoline hydrobromide. One preferred amide is 2-piperidino-1,3,2-dioxaphospolane.
Claims8
The process for converting a penicillin G or V sulfoxide ester to the corresponding 3-desacetoxycephalosporin ester which comprises heating a solution of the penicillin G or V sulfoxide ester in an inert solvent in the presence of a catalyst, said catalyst being the complex formed by a phosphite or phosphine amide selected from the group consisting of:
- 2-piperidino-1,3,2-dioxaphospholane,
- Piperidino-diphenylphosphine,
- 2-piperidino-4,5-benzo-1,3,2-dioxaphospholane,
- 2-(2',6'-dimethylpiperidino-4,5-benzo-1,3,2-dioxaphospholane
- 2-(1'-imidazolyl)-4,5-benzo-1,3,2-dioxaphospholane, tris-(dimethylamino)-phosphine.
- and the salt of a strong acid with a nitrogeneous base selected from the group consisting of:
- alfa-picoline hydrobromide
- alfa-picolinium methanesulfonate
- pyridinium 2-trichloroethylphosphate
- N,n-dimethylaniline hydrobromide
Dependencies are inferred from the claim text.