1,2-Dichloroethane → N-(2(S)-ACETYLTHIOMETHYL-3-(2-METHYLPHENYL)-PROPANOYL)-alpha-PHENYL-beta-ALANINE ETHYL ESTER

Participants

Reaction Steps

Combine α-phenyl-β-alanine ethyl ester, hydrochloride (0.40 g, 1.7 mmol) with 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (0.44 g, 1.77 mmol), HOBT (0.26 g, 1.7 mmol) and triethylamine (0.25 g, 2.6 mmol) in 15 ml DMF. Add EDC (0.32 g, 1.7 mmol), stir 18 hr., partion with EtOAc-water, and wash with 1N HCl, then NaHCO3. Chromatograph on silica, eluting with 1:1 Et2O-hexane, to obtain the title compound, a 1:1 mixture of diastereomers, as an oil, [α]D26 =-19.9° (EtOH).

Provenance & Evidence