4-Methylmorpholine → 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine N-methyl amide

Participants

Reaction Steps

Combine (L)-phenylalanine N-methyl amide trifluoroacetic acid salt (0.22 g, 0.75 mmol) and N-methylmorpholine (0.09 mL, 0.83 mmol) in dichloromethane (5 mL). After 15 minutes, add 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanine (0.18 g, 0.45 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.086 g, 0.45 mmol) and hydroxybenzotriazole (0.060 g, 0.45 mmol). After 18 hours, partition the reaction mixture between ethyl acetate and an aqueous 5% sulfuric acid solution. Separate the layers, extract the organic layer with a saturated sodium bicarbonate solution and then brine. Dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 4% methanol/dichloromethane to give the title compound.

Provenance & Evidence