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US 4,301,072 AGranted
Process for preparing aminopenicillins
AssigneeAmerican Home Products Corporation
InventorReinhold H. W. Bender
Life of this patent
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Abstract
Amide-type Dane salts having the formula: ##STR1## wherein R is a group of the formula: ##STR2## wherein R.sub.2 is hydrogen and R.sub.3 is phenyl or substituted phenyl, R.sub.1 is cyano or nitro, and M is hydrogen, an alkali metal or a triloweralkylamine are disclosed, as well as a process for preparing .alpha.-aminopenicillins from these salts and 6-APA.
Claims3
A process for preparing an .alpha.-amino-penicillin having the formula:
- ##STR13## wherein R is a group having the formula:
- ##STR14## wherein R.sub.2 is hydrogen and R.sub.3 phenyl or substituted phenyl and physiologically acceptable salts thereof, which comprises reacting a silylated 6-amino-penicillanic acid, prepared by reacting 6-amino-penicillanic acid in a dry, inert water-insoluble solvent with a dihalodialkylsilane, at a temperature at or below -20.degree. C. with at least 0.8 equivalents of a mixed anhydride prepared by reacting an amide-type Dane salt having the formula:
- ##STR15## wherein R is as defined hereinbefore and R.sub.1 is cyano or nitro and M is an alkali metal or a triloweralkylamine, with an alkylchlorocarbonate, in the presence of a catalyst, in methylene chloride containing as cosolvent at least 10% by volume of dimethylacetamide having a water content of 4-5%, to yield an N-protected aminopenicillin, hydrolyzing the N-protected aminopenicillin to yield an .alpha.-aminopenicillin and a .beta.-ketoamide, and recovering the .alpha.-aminopenicillin and the .beta.-ketoamide.
Dependencies are inferred from the claim text.