Studies on the reactivity of azetidin-2-ones in phosphate buffer
1H NMR (500 MHz) analyses reveal that in phosphate buffer, N-arylsulfonyl β-lactams such as ethyl N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate and (4S)-ethyl 3-ethyl-N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate undergo hydrolysis through (minimally) two mechanisms: via direct hyd...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
1997
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| Summary: | 1H NMR (500 MHz) analyses reveal that in phosphate buffer, N-arylsulfonyl β-lactams such as ethyl N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate and (4S)-ethyl 3-ethyl-N-(p-nitrophenylsulfonyl)-2-oxoazetidine-4-carboxylate undergo hydrolysis through (minimally) two mechanisms: via direct hydrolysis and via an unstable acyl phosphate intermediate. The acyl phosphate intermediates can be trapped using hydrazine. |
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