Methanol → Methyl L-phenylalaninate hydrochloride

Participants

Reaction Steps

A suspension of 16.52 g (100 mmol) of L-phenylalanine in 200 ml of anhydrous methanol was cooled in a ice-salt bath. Thionyl chloride (23.8 g, 200 mmol) was added dropwise over a period of 30 minutes. After the addition was completed, cooling was stopped and the reaction mixture was stirred at 25° for 20 hours. After heating under reflux for 30 minutes, the solution was cooled and freed of solvent on a rotary evaporator under reduced pressure to yield 21.29 g (98%) of L-Phe-OMe-HCl. TLC: Rf 0.87 (10% MeOH in CHCl3, few drops of NH4OH).

Provenance & Evidence