2-Aminothiazole → HCID 58697916, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2(R)-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-2-yl)-propionic acid (80 mg, 0.26 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluoro-phosphate (177 mg, 0.40 mmol), and 2-aminothiazole (40 mg, 0.40 mmol) in methylene chloride (10 mL) at 25° C. was treated with triethylamine (0.11 mL, 0.79 mmol). The resulting reaction mixture was stirred at 25° C. for 16 h. The reaction mixture was then diluted with water (10 mL) and extracted with methylene chloride 3×10 mL). The combined organic layers were sequentially washed with water (1×10 mL), a 1N aqueous sodium hydroxide solution (1×10 mL), a 1N aqueous hydrochloric acid solution (1×10 mL), and a saturated sodium chloride solution (1×10 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95/5 hexanes/ethyl acetate to 70/30 hexanes/ethyl acetate) afforded the 2(R)-(3,4-dichloro-phenyl)-3-(tetrahydro-pyran-2-yl)-N-thiazol-2-yl-propionamide (57 mg, 57%) as a white foam: EI-HRMS m/e calcd for C17H18Cl2N2O2S (M+) 384.066. found 384.1467.

Provenance & Evidence