trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl )azetidine-1-oxide

trans-3-Benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was prepared by stereoselective oxidation of the corresponding azetidine precursor. The stable molecule was characterized in a low-polarity solution by IR, H-1-NMR and C-13-NMR, and in the solid state as a co-crystal with water by X-Ray diffraction. The N-oxide function made a strong intramolecular 7-membered ring hydrogen bond with the methyl amide NH in solution and formed an intermolecular H-bond with the carbamate NH in a neighboring molecule in the solid state.

Automated summary

In this study, trans-3-benzyloxycarbonylamino-1-methyl-3-(methylcarbamoyl)azetidine-1-oxide was successfully synthesized by stereoselective oxidation. The stable molecule was characterized in solution and solid state, revealing different intramolecular and intermolecular hydrogen bonding patterns.