Triethylamine → Methyl bis-(cyclohexylmethyl)acetyl-(alpha-methyl-D-tryptophan)

Participants

Reaction Steps

To a solution of 0.69 g (3.0 mmol) of methyl α-methyl-D-tryptophan in 20 mL THF was added 0.8 g (3.0 mmol) of bis-(cyclohexylmethyl)acetyl chloride followed by 0.5 mL of Et3N and the suspension stirred at room temperature for 3 days. The mixture was diluted with EtOAc and washed with 1N citric acid, H2O, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 1.4 g of the crude product as a foam. Chromatography on silica gel, eluting with CHCl3 /EtOAc (95/5) gave 0.91 g (65% yield) of the product as a white foam. The structure was confirmed by NMR and mass spectroscopy.

Provenance & Evidence