Claims
- 1. A process for preparing an .alpha.-aminopenicillin having the formula: ##STR9## wherein R is a group having the formula: ##STR10## wherein R.sub.2 is phenyl or substituted phenyl, and physiologically acceptable salts thereof, which comprises reacting a derivative of 6-aminopenicillanic acid in an aqueous solution at a temperature at or below -20.degree. C. with at least 0.8 equivalent of a mixed anhydride prepared by reacting an amide-type Dane salt having the formula: ##STR11## wherein R is a defined hereinbefore and R.sub.1 is cyano or nitro and M is an alkali metal or triloweralkylamine, with an alkyl- or aralkylchlorocarbonate in the presence of a catalyst in a mixture of acetone and dimethylformamide or dimethylacetamide, adding thereto methylene chloride, hydrolyzing the resulting N-protected aminopenicillin to yield an .alpha.-aminopenicillin and a .beta.-ketoamide, and recovering the .alpha.-aminopenicillin and the .beta.-ketoamide.
- 2. The process of claim 1, wherein said recovered .beta.-ketoamide is recycled for preparation of the amide-type Dane salt.
- 3. The process of claim 1, wherein said mixed anhydride is prepared at a temperature of -10.degree. C. or below.
- 4. The process of claim 1, wherein said catalyst is N-methylmorpholine.
- 5. The process of claim 1, wherein said 6-aminopenicillanic acid derivative is an alkali metal, an alkaline earth metal or a trialkylamine salt of 6-aminopenicillanic acid.
- 6. The process of claim 1, wherein the product .alpha.-aminopenicillin is 6-[D(-)-.alpha.-amino-p-hydroxyphenylacetamido]penicillanic acid.
- 7. The process of claim 1, wherein the product .alpha.-aminopenicillin is 6-[D(-)-.alpha.-aminophenylacetamido]penicillanic acid.
Parent Case Info
This is a continuation-in-part of Ser. No. 210,495 filed Nov. 26, 1980, now abandoned, which is a continuation of Ser. No. 067,632 filed Aug. 17, 1979, now abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
3316247 |
Fosker et al. |
Apr 1967 |
|
3325479 |
Fosker et al. |
Jun 1967 |
|
3971775 |
Cowley et al. |
Jul 1976 |
|
4128547 |
van der Drift et al. |
Dec 1978 |
|
Continuations (1)
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Number |
Date |
Country |
Parent |
67632 |
Aug 1979 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
210495 |
Nov 1980 |
|