Sarcosine → HCID 66582435, compound

Participants

Reaction Conditions

Reaction Steps

To a flame-dry 50-mL round-bottomed flask was added 2-methyl-N-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-1-propanesulfonamide (0.100 g, 0.176 mmol, Example 210), N-methylglycine (3.0 mg, 0.040 mmol, Aldrich, St. Louis, Mo.), CuI (0.02 g, 0.09 mmol, Aldrich, St. Louis, Mo.), and potassium phosphate (0.08 g, 0.37 mmol, Aldrich, St. Louis, Mo.). After the mixture was stirred for 10 min, iodobenzene (0.030 g, 0.14 mmol, Aldrich, St. Louis, Mo.) and DMF (3.0 mL) were added. The resulting mixture was heated at 110° C. for 24 h. Additional CuI was added (7.0 mg, 0.035 mmol) and the reaction was heated at 110° C. for an additional 6 d. The reaction mixture was allowed to cool to room temperature and filtered through a pad of Celite® (diatomaceous earth). The filtrate was concentrated and the crude product was purified by column chromatography (24 g of silica gel, 20 to 40% EtOAc in hexanes) to afford 2-methyl-N-phenyl-N-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-1-propanesulfonamide (0.032 g) as a mixture of two isomers:

Provenance & Evidence