4-Toluenesulfonyl chloride → HCID 178480573, compound

Participants

Reaction Steps

To a solution of the product from Step F (0.78 g, 2.52 mmol) and triethylamine (1.02 g, 10.1 mmol) in anhydrous THF (30 mL) at ambient temperature was added tosyl chloride (0.961 g, 5.04 mmol). After stirring for 4.5 h, morpholine (2 mL) was added and the mixture was stirred for 1 h followed by heating at reflux temperature for 10 min. The volatiles were evaporated and a saturated solution of sodium bicarbonate (80 mL) was added. This mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried (MgSO4) and evaporated to a viscous oil which was purified by column chromatography (silica, 5% to 10% methanol/methylene chloride) to give a solid (0.41 g 43%). Recrystallization from ethyl acetate/methylene chloride gave a yellowish solid: mp 192°-194° C. Analysis. Calculated for C12H17N3O5S3 : C, 37.98; H, 4.52; N, 11.07. Found: C, 38.09; H, 4.53; N, 11.09.

Provenance & Evidence