tert-Butyl hydroperoxide → HCID 178462427, compound

Participants

Reaction Steps

A solution of (1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl 2-hydroxyacetate (343.2 mg, 0.571 mmol) obtained from Example 39 in dichloromethane (10 ml) was cooled to 0° C., and to the solution were added tetrazole (80.1 mg, 1.15 mmol) and bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219, (1989); 182.1 mg, 0.742 mmol). The mixture was stirred at the same temperature for 20 minutes. To the mixture was added methanol (0.1 ml), and the mixture was stirred for 5 minutes. To the mixture was added tert-butyl hydroperoxide (80% di-tert-butyl hydroperoxide solution; 0.27 g, 2.4 mmol) at 0° C., and the mixture was stirred at room temperature for 15 minutes. To the mixture were added a saturated aqueous solution of sodium hydrogen carbonate and a solution of sodium thiosulfate, and the mixture was stirred for 10 minutes. At the end of this time, the product was extracted with ethyl acetate, and the solvent was removed under reduced pressure. The resulting oily residue was purified by column chromatography using silica gel (20 g; eluent, ethyl acetate:hexane=4:1), to give the title compound (365.4 mg, yield 84%) as a pale brown amorphous solid.

Provenance & Evidence