Peracetic Acid → 3[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-4-methyl-3-methylsulphinylazetidin-2-one

Participants

Reaction Steps

The azetidinone (60) (250 mg) in dry dioxan (10 ml) was treated with a (5.07% w/v) solution of peracetic acid in acetic acid (0.69 ml) for 1.5 hour. The solvent was then evaporated in vacuo, the complete removal of acidic residues being ensured. Silica gel chromatography of the residue gave the title compound as a pale-white solid (149 mg), νmax. (Nujol) 3300, 1760, 1710, and 1670 cm-1, δ[(CD3)2SO] 0.65, 0.93, 1.16 and 1.19 (each d, J 6.5 Hz, together 3H), 1.07 (t, J 7 Hz, 3H), 1.99, 2.14, 2.39, 2.64 and 2.68 (each s, together 3H), 3.37 (q, J 7 Hz, 2H), 3.47-3.52 (m, 2H), 3.79-3.92 (m, 2H), 3.92-4.10 (complex m, together 1H), [5.45-5.60 (complex m) and 5.86 (d, J 7 Hz), together 1H], 7.27-7.55 (m, 5H), 8.63 and 8.74 br (each s, together 1H, exch), 9.14 and 9.35 br (each s, together 1H, exch.), and 9.65-10.00 (complex m, together 1H, exch).

Provenance & Evidence