Aluminium lithium hydride → 3-cyclopentyl-N-[4-(2-hydroxy-ethyl)-thiazol-2-yl]-2-(4-phenoxy-phenyl)-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of {2-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester (prepared in Example 12B-a, 86 mg, 0.18 mmol) in diethyl ether (5 mL) was cooled to 0° C. and then treated with lithium aluminum hydride (10 mg, 0.27 mmol). The reaction mixture was slowly warmed to 25° C. where it was stirred for 16 h. At this time, the reaction mixture was slowly diluted with water (5 mL) and then extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 70/30 hexanes/ethyl acetate) afforded 3-cyclopentyl-N-[4-(2-hydroxy-ethyl)-thiazol-2-yl]-2-(4-phenoxy-phenyl)-propionamide (21 mg, 27%) as an off-white solid: FAB-HRMS m/e calcd for C25H28N2O3S (M+H)+ 437.1899, found 437.1900.

Provenance & Evidence