Triethylamine → HCID 22285722, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product from Step F (0.77 g, 2.4 mmol) in dichloromethane (10 mL) was added triethylamine (0.40 mL, 2.9 mmol) followed by methanesulfonyl chloride (0.22 mL, 2.9 mmol) at 0° C. After 30 min, dichloromethane (50 mL) was added followed by water (50 mL). The organic layer was separated and the aqueous was extracted with dichloromethane (2×50 mL). The combined extracts were washed with brine (30 mL), dried (MgSO4), and evaporated to a residue that was taken up in DMF (6 mL) and sodium azide (0.33 g, 5.0 mmol) was added. The reaction mixture was heated at 70° C. for 17 h, poured into water, and extracted with ether (3×50 mL). The combined extracts were washed with brine, dried (MgSO4), and evaporated to a residue that was purified by column chromatography (silica, hexane to 10% ethyl acetate in hexane) to give an oil (0.75 g, 90%): MS (ES) m/z 348 (M+).

Provenance & Evidence