Tetrabutylammonium Fluoride → HCID 89444237, compound

Participants

Reaction Steps

To a solution of methyl 4-[[5-[(Z)—N′-acetoxycarbamimidoyl]-2-pyridyl]amino]-4-oxo-butanoate (obtained in step 2, 0.18 g, 0.58 mmol, 1 equiv.) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride (1.0 mol/L) in THF (0.053 g, 0.058 mL, 0.058 mmol, 0.1 equiv.) at room temperature. The mixture was stirred for 4 h at room temperature. The residue was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried on magnesium sulfate, and then concentrated under vacuum. The residue was purified by flash chromatography, eluted with a gradient of ethyl acetate and cyclohexane to give methyl 4-[[5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-pyridyl]amino]-4-oxo-butanoate A75 (0.062 g, 37% yield). LC-MS (Method F) RT 0.72, 291 (M+H+).

Provenance & Evidence