Ethyl Acetate → HCID 10183718, compound

Participants

Reaction Conditions

Reaction Steps

A solution of {2-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester (prepared in Example 5B-b, 60 mg, 0.117 mmol) in diethyl ether (1 mL) was cooled to 0° C. and then slowly treated with lithium aluminum hydride powder (6.7 mg, 0.176 mmol). The reaction mixture was stirred at 0° C. for 30 min, at which time, thin layer chromatography showed the absence of starting material. The reaction mixture was slowly quenched by the dropwise addition of a saturated aqueous sodium bicarbonate solution (2 mL). The resulting reaction mixture was treated with ethyl acetate (2 mL) and allowed to stir at 25° C. for 15 h. The two-phase reaction mixture was then partitioned between water (20 mL) and ethyl acetate (20 mL), and the layers were separated. The aqueous layer was further extracted with ethyl acetate (1×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/2 hexanes/ethyl acetate) afforded 3-cyclopentyl-N-[4-(2-hydroxyethyl)-thiazol-2-yl]-2-(4-naphthalen-1-yl-phenyl)-propionamide (19 mg, 34%) as a yellow foam: mp 84-87° C.; EI-HRMS m/e calcd for C29H30N2O2S (M+) 470.2028, found 470.2020.

Provenance & Evidence