Pyridine → [cis-2-[[(Acetylamino)oxy]methyl]-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl ester

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Reaction Steps

To the oxyamine produced in Example 1 (400 mg, 1.73 mmol) dissolved in a solution of CH2Cl2 -DMF (1:1) at 0° C. was added pyridine (1.1 eq.) followed by acetyl chloride (1.1 eq.). The reaction was allowed to stir for 15 minutes followed by removal of the solvents under reduced pressure. The residue obtained was purified by flash chromatography (5% CH3OH in CH2Cl2 to 10% CH3OH in CH2Cl2) to afford [cis-2-[[(acetylamino)oxy]methyl]-4-oxo-3-azetidinyl]carbamic acid 1,1-dimethylethyl ester (418 mg, 88.6%): IR (KBr) 3290, 2980, 1760, 1690, 1365, and 1160 cm-1 ; NMR (80 MHz, DMSO-d6) δ 1.40 (9H, s), 1.73 (3H, s), 3.83 (3H, m), 4.90 (1H, dd, J=9, 5 Hz), 7.60 (1H, d, J=9 Hz, exchangeable), 8.55 (1H, s, exchangeable); FAB HRMS, m/e 274.1400 (MH+ calculated for C11H20O5N3 : 274.1403).

Provenance & Evidence