Benzofuran → HCID 18517728, compound

Participants

Reaction Conditions

Reaction Steps

A solution comprised of benzofuran (0.302 g, 2.56 mmol) in anhydrous ether (5 mL) was cooled to −15° C. under a nitrogen atmosphere and then a solution of n-butyllithium (1.6 mL in hexanes) was added dropwise over 2 minutes. The mixture was stirred for 1 hour and then a solution comprised of benzyl 1-[1-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamoyl]-3-methylbutylcarbamate (0.3 g, 0.64 mmol) in diethyl ether was added. The mixture was stirred at −15° C. until the reaction was complete. The mixture was quenched with a solution of acetic acid (0.153 mL) in diethyl ether (50 mL). The organic phase was washed with brine (40 mL), dried (MgSO4) and concentrated in vacuo. The product was purified from the residue by flash chromatography eluting with 2:3 ethyl acetate/hexanes to provide benzyl 1-[1-(benzofur-2-ylcarbonyl)-3-phenylpropylcarbamoyl]-3-methylbutylcarbamate (70 mg, 0.13 mmol) as a white solid. 1H NMR (CDCl3): δ 0.8-0.99 (d, J=4 Hz, 6H), 1.5 (m, 1H), δ 1.6-1.72 (m, 2H), δ 1.99-2.18 (m, 1H), δ 2.22-2.41 (m, 1H), δ 2.6-2.75 (m, 2H), δ 4.21 (m, 1H), δ 5.01 (m, 1H), δ 5.17 (s, 2H), δ 5.50 (m, 1H), δ 6.75-6.81 (d, J=7 Hz, 1H), δ 7.10-7.37 (m, 11H) 7.4-7.59(m, 3H), δ 7.64 (d, J=7 Hz, 1H). (C32H34N2O5).

Provenance & Evidence