4-Methylmorpholine → N-[2(S)-Acetylthiomethyl-3-(2-methylphenyl)-propanoyl]-(S)-isoserine ethyl ester

Participants

Reaction Steps

Combine 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (1.65 g) and (S)-isoserine ethyl ester hydrochloride (1.10 g), EDC (1.51 g), HOBT (0.99 g) and N-methylmorpholine (1.50 ml) in DMF (10 ml), and stir the resulting mixture for 20 hours. Concentrate the reaction mixture in vacuo and partition the residue between dichloromethane/water. Concentrate the dried (MgSO4) dichloromethane solution in vacuo. Chromatograph the resulting residue on a column of flash silica gel (300 ml) using ethyl acetate:hexane (1:3); ethyl acetate; ethyl acetate:methanol (9:1) as eluant to give the title compound, a colorless oil, [α]D26 =0° (MeOH).

Provenance & Evidence