Water → HCID 86588455, compound

Participants

Reaction Steps

4-(Oxazole-4-carbonyl-1-((S)-1-phenylethyl)pyrrolidin-2-one (0.5 g, 1.76 mmol) [Example 6B1] and O-benzylhydroxylamine, hydrochloride (0.42 g, 2.64 mmol) in pyridine (5 mL) were refluxed for five hours and then cooled to room temperature. The reaction mixture was diluted with water, washed with saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with a mixture of 1:2 mixture of hexanes:ethyl acetate to provide 0.41 g of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.75-7.60 (m, 1H), 7.40-7.12 (m, 11H), 5.60-5.45 (m, 1H), 5.35-5.23 (m, 1H), 5.20-5.08 (m, 1H), 4.30-4.16 (m, 1H), 3.88-2.60 (m, 4H), 1.50-1.30 (m, 3H).

Provenance & Evidence