Synthesis of Selective β-Lactam Derivatives
In this work, the mild conditions of Mitsunobu reaction were used to convert the hydroxyl group of 6-triphenylmethylaminopenicillanyl alcohol to amines by using different nuleophiles such as phthalimide, di-tert-butyliminodicarboxylate and potassium cyanate. The existence of the β-lactam carbonyl gr...
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| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
An-Najah National University
2012-11-01
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| Series: | مجلة جامعة النجاح للأبحاث العلوم الطبيعية |
| Online Access: | https://journals.najah.edu/media/journals/full_texts/synthesis-selective-b-lactam-derivatives.pdf |
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| Summary: | In this work, the mild conditions of Mitsunobu reaction were used to convert the hydroxyl group of 6-triphenylmethylaminopenicillanyl alcohol to amines by using different nuleophiles such as phthalimide, di-tert-butyliminodicarboxylate and potassium cyanate. The existence of the β-lactam carbonyl group increased the instability towards nucleophilic attack of refluxing methanol and the four-membered ring was opened. Treating 3-Di-tert-Butoxycarbonylaminomethyl-6-triphenylmethylamino - penicillanate with 50% trifluoroacetic acid in dichloromethane, resulted in the cleavage of triphenylmethyl group and one tert-butyl group. While the removal of both triphenylmethyl groups as well as di-tert-butylamino carbonyl group occurred when 75% trifluoroacetic acid was used. The significance of this study is to synthesize β-lactam derivatives that might to be more resistant to degradation by β-lactamase and hence, therapeutically more effective. |
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| ISSN: | 1727-2114 2311-8865 |