Dicyclohexylcarbodiimide → HCID 53775475, compound

Participants

Reaction Steps

1.24 g of dicyclohexylcarbodiimide was added to 30 ml Of a solution of 1.77 g of N-benzyloxy-DL-tryptophane and 0.70 g of N-hydroxysuccinimide in anhydrous dioxane, with ice-cooling. The mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered to remove the insoluble materials, whereby a light brown solution was obtained. Separately, 0.8 ml of triethylamine was added to 20 ml of a suspension of 0.89 g of methyl L-serinate hydrochloride in anhydrous dioxane. The mixture was stirred at room temperature for 2 hours. Thereto was added the above light brown solution. The resulting mixture was stirred at room temperature for 66 hours. The reaction mixture was diluted with 200 ml of ethyl acetate. The resulting solution was washed with 1N hydrochloric acid and an aqueous solution saturated with sodium chloride, then dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent, to obtain 2.07 g of methyl (N-benzyloxy-DL-tryptophyl)-L-serinate as a brown oily substance.

Provenance & Evidence