Acetyl chloride → HCID 66582340, compound

Participants

Reaction Steps

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-((phenylamino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.130 g, 0.247 mmol, Example 203) in CH2Cl2 (3.0 mL) was added 4-dimethylaminopyridine (6.1 mg, 0.049 mmol), Hünig's base (0.129 mL, 0.742 mmol), and acetyl chloride (0.035 mL, 0.49 mmol, Aldrich, St. Louis, Mo.). The resulting mixture was stirred at room temperature for 30 min and then the solvent was removed in vacuo. The residue was purified by column chromatography (24 g of silica gel, 10% to 40% EtOAc in hexanes) to afford N-phenyl-N-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)acetamide (0.032 g) as a mixture of two isomers:

Provenance & Evidence