Sodium Thiosulfate → HCID 178433054, compound

Participants

Reaction Steps

{4-[6-(trans-4-tert-Butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol (227 mg, 0.000490 mol) was treated with di-tert-butyl N,N-diethylphosphoramidite (545 μL, 0.00196 mol, Aldrich), 1H-tetrazole (177 mg, 0.00253 mol, ChemPacific) in tetrahydrofuran (10.0 mL, Aldrich) overnight. m-Chloroperbenzoic acid (570 mg, 0.00198 mol) was added to a cooled solution (ice bath) and the reaction was stirred at room temperature for 1 hour. Sodium thiosulfate was added as a 10% solution in saturated sodium bicarbonate (10 mL) and the reaction stirred for 2 h. The reaction was evaporated. The mixture was partitioned between methylene chloride and water/saturated sodium bicarbonate. The organic layer was further washed once with water and then dried with magnesium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography on a column pre-treated with 1% triethylamine/methylene chloride, then eluted with 0-10% methanol in methylene chloride. Concentrating appropriate fractions gave the product in 234 mg yield (73%).

Provenance & Evidence