Triethylamine → HCID 86760620, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product from Step B (1.8 g, 7.6 mmol) in dichloromethane (10 mL) was added triethylamine (1.3 mL, 9.2 mmol) followed by methanesulfonyl chloride (0.72 mL, 9.2 mmol) at 0° C. After 30 min, ether (50 mL) was added followed by water (50 mL). The organic layer was separated and the aqueous was extracted with ether (2×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated. The residue was taken up in DMF (20 mL) and sodium azide (0.99 g, 15.2 mmol) was added. The reaction mixture was heated at 70° C. for 14 h, poured into water, and extracted with ether (3×50 mL). The combined extracts were washed with brine, dried and evaporated. The residue was purified by chromatography (silica, hexane to 10% ethyl acetate in hexane) to give an oil (1.75 g, 83%): MS (ES) m/z 274 (M+); 1H NMR (CDCl3) 8.22 (1H, s), 8.09 (1H, s), 7.84 (1H, d, J=1.2 Hz), 7.78 (1H, d, J=1.2 Hz), 4.45 (4H, m), 4.24 (1H, m), 1.46 (3H, t, J=7.2 Hz). 1.35 (3H, d, J=6.8 Hz).

Provenance & Evidence