4-Iodoaniline → [2-(4-Iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 4-iodoaniline (2.0 g, 9.17 mmol), 3-tert-butoxycarbonylaminopropionic acid (1.61 g, 8.49 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.95 g, 10.19 mmol), 1-hydroxy-7-azabenzotriazole (0.12 g, 0.85 mmol), and DMF (20 mL), was stirred at room temperature for 72 hours. The solvent was evaporated in vacuo. The residue was dissolved in methylene chloride (100 mL) and washed with 10% citric acid (2×50 mL), then 10% aqueous K2CO3 (2×50 mL). The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3:1, v/v hexanes/ethyl acetate, then 1:1 hexanes/ethyl acetate) to provide 310 (2.44 g, 69%). 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 2.60 (t, 2H), 3.49 (q, 2H), 7.36 (d, 2H), 7.60 (d, 2H).

Provenance & Evidence