Dichloromethane → HCID 19919837, compound

Participants

Reaction Steps

To a solution of trifluoromethanesulfonic anhydride (0.094 mL, 0.56 mmol) in methylene chloride (10 mL) at -78° C. was added a solution of methyl 4-(hydroxymethyl)benzoate (0.093g, 0.56 mmol) and N,N-diisopropylethylamine (0.098 mL, 0.56 mmol) in methylene chloride (10 mL) dropwise over 5 minutes. This solution was stirred for 15 minutes and then a solution of Z-1,3-dibutyl-5-[[2-butyl-3-(triphenylmethyl)-3H-imidazol-5-yl]methylene]-2,4imidazolidinedione (0.330g, 0.56 mmol) in methylene chloride (5 mL) was added dropwise. The mixture was allowed to slowly warm to room temperature within the cooling bath overnight. Glacial acetic acid (10 mL) and water (2 mL) were added and the mixture boiled for 1 hour on a steam bath. After evaporation in vacuo the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 and brine, and then dried over MgSO4. Chromatography eluting with CHCl3 afforded the required product with spectral characteristics identical with the product formed in Example 33

Provenance & Evidence