2-Aminothiazole → HCID 12050062, compound

Participants

Reaction Steps

A solution of 2(R)-biphenyl-4-yl-3-cyclopentylpropionic acid (36.9 mg, 0.13 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (52.3 mg, 0.14 mmol), N,N-diisopropylethylamine (66 μL, 0.38 mmol), and 2-aminothiazole (25.1 mg, 0.25 mmol) in dry N,N-dimethylformamide (627 μL) was stirred at 25° C. under nitrogen for 13 h. The reaction mixture was concentrated in vacuo to remove the N,N-dimethylformamide. The resulting residue was diluted with ethyl acetate (100 mL). The organic layer was washed with a 10% aqueous hydrochloric acid solution (1×100 mL), a saturated aqueous sodium bicarbonate solution (1×100 mL), and a saturated aqueous sodium chloride solution (1×100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded (2R)-2-biphenyl-4-yl-3-cyclopentyl-N-thiazol-2-yl-propionamide (29.4 mg, 62%) as a white foam: mp 132-134° C.; FAB-HRMS m/e calcd for C23H24N2OS (M+H)+ 377.1687, found 377.1696.

Provenance & Evidence