Thionyl Chloride → HCID 89443899, compound

Participants

Reaction Steps

To a solution of butan-1-ol (3 mL) was added dropwise thionyl chloride (2.73 mmol, 0.200 mL 3 eq). After 5 min, 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoic acid A2 (prepared as described before, 200 mg, 0.912 mmol) was added to the solution. The reaction mixture was stirred overnight at room temperature. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer was washed with a saturated solution of sodium hydrogenocarbonete and dried on magnesium sulfate, then concentrated under vacuum. The residue was first washed with cyclohexane and the solid obtained was purified by flash chromatography eluting with cyclohexane-ethyl acetate to give butyl 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoate A66 (10%) and the by-product butyl 6-[(4-butoxy-4-oxo-butanoyl)amino]pyridine-3-carboxylate A67 (9%).

Provenance & Evidence