Pyridine → 3[2-(4-Ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-phenylacetamido]-3-formamido-4-methylazetidin-2-one

Participants

Reaction Steps

A solution of the amine (62) (87 mg) and pyridine (33 mg) in dry dichloromethane (2 ml) was treated with formic acetic anhydride (40 mg) for 24 hour after which time the solvent was removed in vacuo. Dry dioxan was added and solution re-evaporated (×3). Silica gel column chromatography of the residue gave the title compound (63) (80 mg) as a white powder, νmax. (Nujol) 3500, 3250, 1770, 1710, 1670, and 1500 cm-1, δ[(CD3)2CO]0.88, 0.96, 1.00 and 1.03 (each d, J 6.5 Hz, together 3H) (irradiation at 4.00 caused the signals centered at 0.88 and 0.96 to collapse to 2×s), 1.16 (t, J7 Hz, 3H), 3.49 (q, J 7 .Hz, 2H), 3.58-3.68 (m. 2H), 3.93-4.23 (complex m, together 3H), 5.59-5.84 (complex m, together 1H) (collapses to 4×s at 5.65, 5.69, 5.76 and 5.80 upon irradiation at 10.0), 7.25-7.80 (complex m, together 6H) (simplifies on exchange with D2O to a m at 7.25-7.56), 7.97-8.86 (complex m, together 3H) (simplifies to 4×s at 8.03, 8.11, 8.24, and 8.48 on exch.), 9.90-10.05 (m, 1H, exch).

Provenance & Evidence