Sodium hydride → HCID 66817371, compound

Participants

Reaction Steps

Sodium hydride (60% oil suspension, 5.6 mg, 0.14 mmol) was added to a solution of N-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-N-methyl-chloroformamide (30 mg, 50.1 μmol) in tetrahydrofuran (1.0 ml) at 0° C., and the mixture was stirred for 15 minutes. 2-(tert-Butyl-dimethyl-silanyloxy)-ethanol (30 μL, 0.14 mmol) was then added and the mixture was stirred at 40° C. for two hours. The mixture was cooled, and then quenched with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give (3,5-dimethyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-methyl-carbamic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester (29 mg, 78%).

Provenance & Evidence