Allyl Alcohol → HCID 89444286, compound

Participants

Reaction Steps

To a solution of prop-2-en-1-ol (2 mL) was added dropwise thionyl chloride (3 eq, 1.7 mmol). After 5 min, 4-[(5-chloropyrazin-2-yl)amino]-4-oxo-butanoic acid A6 (prepared as described before, 0.13 g, 0.57 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 allyl 4-[(5-chloropyrazin-2-yl)amino]-4-oxo-butanoate A10 (37%). 1H NMR (400 MHz, CDCl3) 9.29 (s, 1H), 8.27 (s, 1H), 8.18 (bs, 1H), 5.92 (m, 1H), 5.29 (m, 2H), 4.62 (m, 2H), 2.80 (m, 4H).

Provenance & Evidence