Triethylamine → HCID 131724352, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step B (0.68 g, 1.88 mmol) and triethylamine (0.76 g, 1.04 mL, 7.51 mmol, 4.0 equiv.) in anhydrous THF (50 ml) at 0° C. was added methanesulfonic anhydride (0.59 g, 3.38 mmol, 1.8 equiv.). The mixture was stirred for 10 min and sodium azide (1.22 g, 18.8 mmol, 10 equiv.) was added. The solvent was removed by evaporation and anhydrous dimethyl sulfoxide (20 mL) was added. This mixture was heated at 95° C. for 3 h, cooled, poured into a saturated solution of sodium bicarbonate (80 mL), and extracted with ethyl acetate (3×60 mL). The combined extracts were dried (MgSO4), filtered, and evaporated to an oil, which was purified by chromatography (silica, 10% ethyl acetate in hexane) to give a solid (0.61 g, 84%): mp 77-78° C.; LC/MS (+ESI) m/z 388 (M+H).

Provenance & Evidence