4-Toluenesulfonyl chloride → HCID 89472108, compound

Participants

Reaction Conditions

Reaction Steps

23 mg (0.11 mmol equivalents) of 2,2-dimethyl-5-hydroxymethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-1,3-dioxane was dissolved in 1.0 mL of triethylamine, 1 mg (0.01 mmol equivalents) of N,N-dimethylaminopyridine and 23 mg (0.12 mmol equivalents) of p-toluenesulfonyl chloride were added thereto, and the mixture was stirred at room temperature (25° C.) for 16 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with ethyl acetate. The combined ethyl acetate layers were dried with anhydrous magnesium sulfate, and then concentrated under vacuum. The obtained crude product was purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=1/3) to give 16 mg (0.03 mmol equivalents) of 2,2-dimethyl-5-[(4-methoxymethoxymethyl-2-nitro-1H-imidazol-1-yl)methyl]-5-(p-toluenesulfonyloxymethyl)-1,3-dioxane.

Provenance & Evidence