Dicyclohexylcarbodiimide → HCID 131716964, compound

Participants

Reaction Steps

Fmoc-Asp(t-Bu)-OH (Bachem Bioscience) (9.04 g, 22 mmoles) and dicyclohexylcarbodiimide (4.12 g, 20 mmoles) were dissolved in dimethylformamide/methylene chloride (1:5; 50 ml) and cooled in an ice bath. The mixture was stirred for 15 minutes and 4-(2-aminoethyl)-pyridine (2.44 g, 20 mmoles) was added. The combined reaction mixture was stirred overnight and the precipitate was filtered. The filtrate was evaporated to dryness. The residue was redissolved in ethyl acetate (300 ml) and washed with saturated sodium bicarbonate solution (3 times), 0.5N HCl (2 times) and water. The organic layer was dried over sodium sulfate, filtered and the filtrate was evaporated to dryness. The residue was treated with 20% diethylamine/methylene chloride (50 ml) for 1.5 hours, and the reaction mixture was evaporated to dryness and used without further purification.

Provenance & Evidence