Hydrogen Peroxide → (2R)-11-[3,17beta-dihydroxyestra-1,3,5(10)-trien-11beta-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanic Acid

Participants

Reaction Steps

(4S,5R)-1-{(2R)-11-[3,17β-Dihydroxyestra-1,3,5(10)-trien-11β-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanoyl}-3,4-dimethyl-5-phenylimidazolidin-2-one (140 mg, 0.16 mmol) was dissolved in DME (3 ml). To this solution, tetra-n-butylammonium hydroxide solution (40% w/w, 312 mg, 0.48 mmol) and aqueous hydrogen peroxide (30% w/w, 56 mg, 0.48 mmol) were added, and the resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was quenched with 10% aqueous sodium sulfite, acidified with 2N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (Wako gel C-200, eluent: ethyl acetate/n-hexane=3/7), then by preparative HPLC (YMC-ODS-5-B (3×25 cm), eluent: acetonitrile/water/ trifluoroacetic acid=90/10/0.1, flow rate: 18 mL/min), to give the desired compound (2R)-11-[3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)undecanic acid (58 mg, Yield 52%).

Provenance & Evidence