Precursor of a β‐lactamase inhibitor: allyl (4S,8S,9R)‐10‐[(E)‐ethylidene]‐4‐methoxy‐11‐oxo‐1‐azatricyclo[7.2.0.03,8]undec‐2‐ene‐2‐carboxylate |
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Authors: | Ivan Leban Lovro Seli
Toma Mesar Anton opar Tom olmajer |
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Institution: | Ivan Leban,Lovro Seli?,Toma? Mesar,Anton ?opar,Tom ?olmajer |
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Abstract: | The molecular structure of the title tricyclic compound, C17H21NO4, which is the immediate precursor of a potent synthetic inhibitor {Lek157: sodium (8S,9R)‐10‐(E)‐ethylidene]‐4‐methoxy‐11‐oxo‐1‐azatricyclo7.2.0.03,8]undec‐2‐ene‐2‐carboxylate} with remarkable potency, provides experimental evidence for the previously modelled relative position of the fused cyclohexyl ring and the carbonyl group of the β‐lactam ring, which takes part in the formation of the initial tetrahedral acyl–enzyme complex. In this hydrophobic molecule, the overall geometry is influenced by C—H?O intramolecular hydrogen bonds 3.046 (4) and 3.538 (6) Å, with corresponding normalized H?O distances of 2.30 and 2.46 Å], whereas the molecules are interconnected through intermolecular C—H?O hydrogen bonds 3.335 (4)–3.575 (5) Å]. |
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