[N-:1]=[N+:2]=[N-:3].[Na+].C(O)(C(F)(F)F)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](O)([CH3:21])[CH3:20])=[CH:15][C:14]=1[CH3:23].N>C(Cl)(Cl)Cl.O>[N:1]([C:19]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[C:14]([CH3:23])[CH:15]=1)([CH3:21])[CH3:20])=[N+:2]=[N-:3]A flask was charged with sodium azide (4.22 g, 65 mmol) and chloroform (250 mL). The mixture was cooled in an ice-salt bath to −5° C. TFA (12.52 mL, 162 mmol) was added over 3 minutes, followed by a solution of the alcohol INT 20 (6 g, 32.5 mmol) in chloroform (10 mL) while the temperature was kept below 0° C. The formed slurry was stirred for one hour, then allowed to warm up to room temperature overnight. After that time, the thick slurry had turned into a cloudy solution. The mixture was treated with concentrated ammonia (25 mL) and water (50 mL). The chloroform layer was separated and the aqueous layer was extracted once more with chloroform. The combined organic extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/CH2Cl2).
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