Toluene → N-Fmoc-di(4-docosoxyphenyl)methylamine

Participants

Reaction Conditions

Reaction Steps

To 4,4′-didocosoxybenzhydrol (713 mg, 856 μmol) were added toluene (15 ml), Fmoc-NH2 (246 mg, 1.03 mmol) and methanesulfonic acid (8.3 μl, 128 μmol), and the mixture was stirred at 100° C. for 3 hours. After confirmation of disappearance of a benzhydrol type anchor, the mixture was cooled to room temperature. 2.5% Aqueous sodium hydrogen carbonate (10 ml) was added, and the mixture was stirred. After partitioning, the organic layer was further washed with water (10 ml×2). The organic layer was evaporated under reduced pressure, and the residue was washed with methanol (10% ml) to give N-Fmoc-di(4-docosoxyphenyl)methylamine (540 mg, 512 μmol, yield 60%).

Provenance & Evidence