2-Aminothiazole → 3-cyclopentyl-2-(4-phenoxy-phenyl)-N-thiazol-2-yl-propionamide

関与物質

反応条件

反応手順

A solution of 3-cyclopentyl-2-(4-phenoxy-phenyl)-propionic acid (50 mg, 0.16 mmol),benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (106 mg, 0.24 mmol), and 2-aminothiazole (21 mg, 0.24 mmol) in methylene chloride (10 mL) at 25° C. was treated with triethylamine (0.067 mL, 0.48 mmol). The reaction mixture was then stirred at 25° C. for 14 h. After this time, the reaction mixture was diluted with water (10 mL) and then extracted with methylene chloride (3×10 mL). The combined organic extracts were then washed with water (1×10 mL), a 1N aqueous sodium hydroxide solution (1×10 mL), and a 1N aqueous hydrochloric acid solution (1×10 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-phenoxy-phenyl)-N-thiazol-2-yl-propionamide (48 mg, 76%) as an off-white solid: mp 154.9-155.1° C.; EI-HRMS m/e calcd for C23H24O2N2S (M+) 392.1558, found 392.1546.

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