Hydrogen Peroxide → HCID 178453568, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (R)-2-(6-(trans-4-cyclohexylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl)-1-hydroxypropan-2-ylcarbamate was then treated with di-tert-butyl N,N-diethylphosphoramidite (66.6 mg, 0.000267 mol) and 1H-tetrazole (23.4 mg, 0.000334 mol) in tetrahydrofuran (2 mL, 0.03 mol) at 23° C. for 8 hours. 9 M of hydrogen peroxide in water (0.0296 mL, 0.000267 mol) was added to the reaction mixture at −20° C., and the reaction mixture was then stirred for 1 hour at 23° C., followed by sodium thiosulfate (52.8 mg, 0.000334 mol) at −30° C. All the excess of solvents were removed, and the residue was purified via chromatography (SiO2, 4 g, 0-35% ethyl acetate/hexanes) to give a pure intermediate (30.3 mg, 80%). 1H NMR (MeOD) δ: 8.11 (d, J=9.3 Hz, 1H), 8.02 (d, J=9.0 Hz, 1H), 7.84 (d, J=1.8 Hz, 1H), 7.62 (dd, J=9.2, 1.9 Hz, 1H), 7.46 (d, J=9.3 Hz, 1H), 4.38-4.49 (m, 1H), 4.34 (br. s., 1H), 4.25-4.31 (m, 1H), 2.17 (d, J=11.3 Hz, 2H), 1.85 (d, J=10.5 Hz, 2H), 1.70-1.79 (m, 6H), 1.60-1.69 (m, 1H), 1.51 (m, 13H), 1.41-1.47 (m, 23H), 0.97-1.32 (m, 2H)

Provenance & Evidence