Methyl iodide → (S)-1-((S)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-((S)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-hydroxypropan-1-one (41 mg, 0.095 mmol) in DMF (2 mL) at 0° C. was added methyl iodide (50 μL, 0.48 mmol) followed by sodium hydride (10 mg, 60%). After stirring at 0° C. for 30 minutes and room temperature for 3 hours, the mixture was treated with saturated NH4Cl (20 mL) and extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to provide the product (40 mg, 940%) as a yellow oil.

Provenance & Evidence