Triethylamine → HCID 91017075, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of the product from Step A (1.40 g, 3.45 mmol) and triethylamine (1.39 g, 1.92 mL, 1.38 mmol, 4.0 equiv.) in anhydrous THF (50 mL) was added methanesulfonic anhydride (1.20 g, 6.90 mmol, 2.0 equiv.). The mixture was stirred for 30 min and sodium azide (2.24 g, 34.5 mmol, 10 equiv.) was added. THF was evaporated and anhydrous dimethyl sulfoxide (50 mL) was added to the residue; this mixture was heated at 85° C. for 2 h. After cooling, the mixture was poured into a saturated solution of sodium bicarbonate (100 mL) and extracted with EtOAc (3×80 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica, gradient, 10% to 25% ethyl acetate in hexane) to give an oil (0.73 g, 49%): LC/MS (+ESI) m/z 432 (M+H).

Provenance & Evidence