Acetyl chloride → HCID 56932772, compound

Participants

Reaction Steps

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-(((1-methylethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.150 g, 0.305 mmol, Example 195, Step 1) in CH2Cl2 (5.0 mL) was added 4-dimethylaminopyridine (7.46 mg, 0.061 mmol), acetyl chloride (0.043 mL, 0.610 mmol), Hünig's base (0.159 mL, 0.915 mmol). The resulting mixture was stirred at room temperature. After 20 min, the solvent was concentrated and the crude product was purified by column chromatography (24 g of silica, 10 to 40% acetone in hexanes) to afford N-(1-methylethyl)-N-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)acetamide as a mixture of two isomers.

Provenance & Evidence