Metaperiodic acid → HCID 15675162, compound

Participants

Reaction Steps

Aqueous 50% w/w periodic acid (6.3 ml, 22 mmol) was added to (3S,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)-3-phthalimido-azetidin-2-one (4.22 g, 10 mmol) in 50% aqueous THF (75 ml) and heated under reflux for 2.5h. The cooled solution was extracted twice with ethyl acetate and the combined extracts washed twice with water then with brine, dried and evaporated to give a colourless solid. The solid was triturated with ether and the title compound filtered off and dried in vacuo (3.151 g, 90%); [α]D -214.3° (c=1.00 CHCl3); νmax (CHCl3) 1785 (sh), 1769, 1727, 1514, 1391, 1250, and 1124 cm-1 ; δH (CDCl3) 3.73 (3H, s), 4.77 (1H, dd, J 6.29, 2.78 Hz), 5.80 (1 H, d, J 5.80 Hz), 6.95 and 7.39 (4H, ABq, J 8.97 Hz), 7.7-8.0 (4H, m) and 9.90 (1H, d, J 2.73 Hz); m/z (EI) 350 (14), 149 (100%).

Provenance & Evidence