Anisole → N-Butyloxycarbonyl-3-{3-[2-(2-ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-thiophene-2-sulfonamide

Participants

Reaction Steps

To a solution of 3-{3-[2-(2-ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (74.5 mg, 0.153 mmol; see step (b)) in TFA (3 mL) was added anisole (150 μL) and the reaction mixture was stirred for 28 h at ambient temperature. The reaction mixture was concentrated in vacuo and dried in vacuo overnight. To the crude product dissolved in CH2Cl2 (7 mL) was added Na2CO3 (72.9 mg, 0.688 mmol), water (2 mL) and butyl chloroformate (33.0 μL, 0.260 mmol), and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was diluted with CH2Cl2 (30 mL) and washed with citric acid (10% aq), brine and water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (8:92) as eluent to give the sub-title compound in 47% yield, over two steps, (38.5 mg, 0.0724 mmol).

Provenance & Evidence