Abstract
Herein, we present the synthesis, origin and characterization of potential impurities of Ampicillin trihydrate, viz. Ampicillinyl-d-phenylglycine (Ph. Eur impurity E) & l-Ampicillin (Ph. Eur impurity B). The impurity Ampicillinyl-d-phenylglycine originates during the preparation of Ampicillin trihydrate, amidation of carboxylic acid of Ampicillin with d-phenylglycine generates Ampicillinyl-d-phenylglycine, the impurity l-Ampicillin may arise due to the presence of traces l-phenylglycine methylester in d-phenylglycine methylester hydrochloride which may result in the formation of l-Ampicillin. A facile synthetic process for these impurities was developed from the commercially available raw materials.
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The data that support this paper were provided in the supplementary material of this article.
Abbreviations
- DCM:
-
Dichloromethane
- TEA:
-
Triethylamine
- DEA:
-
Diethylamine
- MeOH:
-
Methanol
- HCl:
-
Hydrochloric acid
- 6-APA:
-
6-Aminopenicillanic acid
- K2CO3 :
-
Potassium carbonate
- DMF:
-
Drug master file
- IPA:
-
Isopropyl alcohol
- mp:
-
Melting point
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Acknowledgements
The authors are indebted to Aurobindo Pharma Limited for supporting research work. The authors are grateful to the Analytical Research & Chemical Research Departments of Aurobindo Pharma Limited for the co-operation and support.
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Suresh, C., Devi, D.R., Aegurla, B. et al. Synthesis and characterization of potential impurities of Ampicillin trihydrate. Chem. Pap. 77, 7961–7967 (2023). https://doi.org/10.1007/s11696-023-03064-z
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DOI: https://doi.org/10.1007/s11696-023-03064-z