Benzyl Alcohol → benzyl (2S)-3-amino-2-hydroxypropanoate hydrochloride

Participants

Reaction Steps

At 0°-5°, add thionyl chloride (11.0 ml) dropwise to N-(4-methoxybenzyloxycarbonyl)-(S)-isoserine (10.0 g) in benzyl alcohol (100 ml), warm the mixture to room temperature, and stir for 20 hours. 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, a tan solid, m.p. 127°-130° C., [α]D26 =-18.6° (MeOH).

Provenance & Evidence