Triethylamine → HCID 178461707, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product from Step E (0.16 g, 0.70 mmol) and triethylamine (0.28 g, 0.39 mL, 7.51 mmol) in anhydrous THF (50 mL) at 0° C. was added methanesulfonic anhydride (0.24 g, 1.4 mmol). The mixture was stirred for about 30 minutes and an additional 1 eq of methanesulfonic anhydride was added. After 30 minutes sodium azide (1.10 g, 7.0 mmol) was added to the reaction mixture. The THF was evaporated and anhydrous dimethyl sulfoxide (20 mL) was added to the residue, which was heated at 90° C. for 1 hour. The reaction mixture was cooled, poured into a saturated solution of sodium bicarbonate (80 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts were dried (MgSO4), filterd and evaporated to an oil. Chromatography on silica (gradient, 10% to 20% of ethyl acetate in hexane) gave an oil (0.09 g, 51%): LC/MS (+APCI) m/z 256 (M+H).

Provenance & Evidence