4-Toluenesulfonyl chloride → HCID 19434013, compound

Participants

Reaction Steps

To a solution of the product from Step E (2.16 g, 6.39 mmol) and triethylamine (2.58 g, 25.6 mmol) in anhydrous THF (100 mL) at 0° C. was added p-toluenesulfonyl chloride (2.44 g, 12.8 mmol) with stirring. After 1 h the reaction mixture was warmed to ambient temperature and maintained at this temperature for 4 h. Half of the reaction mixture was removed, cooled on an ice bath and morpholine (3 mL) was added with stirring. The reaction mixture was stirred for 18 h and evaporated to a residue which was mixed with ethyl acetate (200 mL); this solution was washed with a saturated solution of sodium bicarbonate (100 mL), dried (MgSO4), filtered and evaporated to a residue which was purified by colunmn chromatography (silica, 4% methanol/methylene chloride) to give a viscous oil which crystalized from methylene chloride/hexane to afford a yellowish solid (0.41 g, 32%): mp 196°-198° C. Analysis: Calculated for C14H21N3O5S3 : C, 41.26; H, 5.19 N, 10.31. Found: C, 41.35; H, 5.10; N, 10.28.

Provenance & Evidence