HCID 10114706, compound → HCID 10181381, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2-biphenyl-4-yl-3-cyclopentyl-propionylamino)-thiazole-4-carboxylic acid ethyl ester (prepared in Example 1B-d, 200 mg, 0.45 mmol) in methanol (4 mL) was treated with concentrated sulfuric acid (2 drops). The reaction mixture was heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The resulting residue was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 2/1 hexanes/ethyl acetate) afforded 2-(2-biphenyl-4-yl-3-cyclopentyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (80 mg, 41%) as a white solid: mp 98-101° C.; FAB-HRMS m/e calcd for C25H26N2O3S (M+H)+ 435.1743, found 435.1752.

Provenance & Evidence