Hydroxyamine hydrochloride → HCID 89443940, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium bicarbonate (1.81 g, 21.4 mmol, 5 equiv.) and hydroxylamine hydrochloride (1.50 g, 21.4 mmol, 5 equiv.) in water (12 mL) was added to an solution of 4-[(5-cyano-2-pyridyl)amino]-4-oxo-butanoic acid A2 (1.00 g, 4.29 mmol, 1 equiv.) in methanol (120 mL) at 80° C. The solution was heated at 80° C. overnight, before being concentrated under vacuum. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL). 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 to give 760 mg of crude product. This crude product was adsorbed over isolute before purification by flash chromatography eluted with a gradient of methanol and dichloromethane (0 to 10% in methanol) to give methyl 4-[[5-[(Z)—N′-hydroxycarbamimidoyl]-2-pyridyl]amino]-4-oxo-butanoate (0.46 g, 1.73 mmol, 40% yield).

Provenance & Evidence