Dicyclohexylcarbodiimide → Methyl bis-(3,4-methylenedioxyphenylmethyl)acetyl-(alpha-methyl-D-tryptophan)

Participants

Reaction Steps

A solution of 1.0 g (3.0 mmol) of bis-(3,4-methylenedioxyphenylmethyl)acetic acid in 20 mL DMF was treated with 0.68 g (3.3 mmol) of DCC and 0.45 g (3.3 mmol) of HOBt. A solution of 0.73 g (3.15 mmol) of methyl α-methyl-D-tryptophan in 20 mL EtOAc was then added and the solution left stirring for 3 days. The mixture was filtered and the solvent removed under reduced pressure. The residue was taken up in EtOAc and washed with 1N HCl, then saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left the crude product. Chromatography on silica gel, eluting with a gradient of 10% EtOAc in hexane to 50% EtOAc in hexane gave 0.78 g (48.8% yield) of the product as a white foam. The structure was confirmed by NMR spectroscopy.

Provenance & Evidence