N#N.[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:14][CH:15]=[C:16]([C:18](Cl)=[O:19])[N:17]=2)[O:8][CH2:7][CH2:6][O:5]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CC(C)=O.O>[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:14][CH:15]=[C:16]([C:18]([N:21]=[N+:22]=[N-:23])=[O:19])[N:17]=2)[O:8][CH2:7][CH2:6][O:5]1In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), this crude 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl chloride was dissolved in acetone (18.0 mL). The solution was cooled to 0° C. and a solution of sodium azide (314 mg, 4.79 mmol) in H2O (2.0 mL) was added over 1 h. The reaction mixture was stirred at 0° C. for 1.5 h then at rt for 45 min. The mixture was concentrated under reduced pressure (coevaporation with toluene) then dissolved in CH2Cl2 and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=0.89 min [M+H]+=281.38.
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