Hydrochloric Acid → HCID 22315236, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid (prepared as in Example 14, 150 mg, 0.439 mmol), triethylamine (0.184 mL, 1.32 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (291 mg, 0.659 mmol), and 2-aminoimidazole sulfate (87 mg, 0.659 mmol) in methylene chloride (4 mL) and N,N-dimethylformamide (1.5 mL) was stirred at 25° C. for 48 h. The reaction mixture was then diluted with water (25 mL), a 1N aqueous hydrochloric acid solution (5 mL), and ethyl acetate (25 mL). The layers were separated, and the organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford a yellow gel. This yellow gel was diluted with methylene chloride (5 mL), and an off-white solid precipitated. The off-white solid was collected by filtration, and then treated with acetone (5 mL). The acetone mixture was heated to a boil, allowed to cool, and then filtered to afford 3-cyclopentyl-N-(1H-imidazol-2-yl)-2-(4-methanesulfonyl-3-nitro-phenyl)-propionamide (25 mg, 14%) as a white solid: mp 243-244° C.; EI-HRMS m/e calcd for C18H22N4O5S (M+) 406.1311, found 406.1311.

Provenance & Evidence