Isopropyl iodide → HCID 56932937, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of sodium hydride (0.0203 g, 0.508 mmol, Sigma-Aldrich, St. Louis, Mo.) in DMF (1 mL) in a 5 mL vial, 5,5-dimethyl-1-(((2s)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-2,4-imidazolidinedione (0.090 g, 0.161 mmol, Example 228) in DMF (total 1.5 mL) was added dropwise at 0° C. The mixture was stirred at 0° C. for 15 min and 2-iodopropane (0.020 mL, 0.20 mmol, Sigma-Aldrich, St. Louis, Mo.) was added dropwise. The cold bath was removed and the mixture was stirred at room temperature for 12 h. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (20 mL). Saturated aqueous NaCl (20 mL) was added and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with saturated aqueous NaCl (80 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (25 g of silica, 0 to 80% EtOAc in hexanes) to afford 5,5-dimethyl-3-(1-methylethyl)-1-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-2,4-imidazolidinedione (0.021 g) as a mixture of two isomers.

Provenance & Evidence