Sulfoxonium, trimethyl-, iodide (1:1) → HCID 86622359, compound

Participants

Reaction Steps

Step BF (4): To a mixture of trimethylsulfoxonium iodide (20.72 g, 94.2 mmol) in THF (175 mL) was added solid potassium t-butoxide (8.792 g, 78.7 mmol) and the mixture was refluxed for 3 h. The mixture was cooled to 0° C., to which a solution of (S)-4-nitrophenyl 2-(benzyloxycarbonylamino)-3-(3,5-dichlorophenyl)propanoate (15.35 g, 31.40 mmol) in THF (70 mL) was added. The mixture was brought to rt, and stirred for 16 h. Solvents were removed in vacuo. Water and EtOAc were then added, and the solid material filtered (Buchner funnel). The yellowish solid was washed with water and hexane until a white solid remained. The solid was dried in a vacuum oven. All liquid layers were combined and extracted 3 times to EtOAc. The combined organic layers were back-extracted with dilute NaOH, washed with brine, dried over MgSO4, and concentrated in vacuo. The combined material was the desired compound (13.40 g, 97% yield). 1H NMR (500 MHz, CDCl3) δ 6.99-7.39 (m, 8H) 5.80 (d, J=7.93 Hz, 1H) 5.01-5.15 (m, 2H) 4.25-4.37 (m, 2H) 3.31 (s, 3H) 3.26 (s, 3H) 2.96 (d, J=6.41 Hz, 2H).

Provenance & Evidence