Water → HCID 22261901, compound

Participants

Reaction Steps

To a solution of (2RS,3RS)-2-((4-chloro-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-3-(4-fluorophenyl)-3-hydroxypropionic acid (2.0 g, 4.71 mmol) in tetrahydrofuran (40 ml) were added diphenylphosphoryl azide (1.12 ml, 5.18 mmol) and triethylamine (0.99 ml, 7.07 mmol), and the mixture was heated under reflux for 3 hrs. The reaction solution was allowed to cool and water (200 ml) was added. The mixture was extracted with ethyl acetate (200 ml×2). The extract was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give (4RS,5SR)-4-((4-chloro-3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (1.72 g, 87%) as a colorless oil. IR ν maxKBrcm−1: 1759, 1514, 1489. Anal. Calcd for C18H13ClF5NO3: C, 51.26; H, 3.11; N, 3.32. Found: C, 51.16; H, 3.13; N, 3.24. 1H-NMR (CDCl3)δ: 2.30 (2H, d, J=6.8 Hz), 4.25 (1H, q, J=6.8 Hz), 5.30 (1H, brs), 5.80 (1H, d, J=8.0 Hz), 5.98 (1H, tt, J=53.0, 3.0 Hz), 6.89 (1H, dd, J=8.0, 2.0 Hz), 6.99 (1H, s), 7.06-7.20 (2H, m), 7.30-7.42 (3H, m).

Provenance & Evidence