Ethanol → (S)-isoserine ethyl ester hydrochloride

Participants

Reaction Steps

At 0°-5°, add thionyl chloride (2.80 ml) dropwise to N-(4-methoxybenzyloxycarbonyl)-(S)-isoserine (5.0 g) in absolute ethanol (100 ml). Heat the mixture under reflux for 1 hour and stir for 20 hours at room temperature. Concentrate the reaction mixture in vacuo and pour the reaction mixture into diethyl ether (300 ml), and filter the solid. Wash the solid with diethyl ether and dry in vacuo to give the title compound, an amber oil, [α]D26 =-19.8° (MeOH).

Provenance & Evidence