Phenyl isocyanate → HCID 87588157, compound

Participants

Reaction Steps

(8E,12E,14E)-7-acetoxy-6,21-dihydroxy-6,10,12,16,20-pentamethyl-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (100 mg, 154 μmol) was dissolved in methylene chloride (2 mL). Triethylamine (64.2 μL, 461 μmol) and phenyl isocyanate (34.0 μL, 312 μmol) were added to the reaction solution. The reaction solution was stirred at room temperature for 25.5 hours. Then, triethylamine (200 μL, 1.43 μmol) and phenyl isocyanate (98.0 μL, 900 μmol) were further added to the reaction solution, and the reaction solution was stirred at room temperature for six hours. The reaction solution was diluted with ethyl acetate (30 mL), and the dilution was washed with saturated aqueous solution of sodium hydrogencarbonate (6 mL) twice, purified water (6 mL) twice, and brine (6 mL). The resulting organic layer was dried over sodium sulfate, and then filtered. The filtrate was concentrated. The concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=4:1→3:1) and thin-layer chromatography (MERCK 60 F254, 0.5 mm, toluene:acetone=5:1) to obtain the title compound (54.0 mg, 70.1 μmol, 45.6%) as a colorless oil.

Provenance & Evidence