[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#N.O=[C:20]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][N:1]1[CH:20]=[C:14]([C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([OH:10])[CH:12]=2)[N:3]=[N:2]1)[CH3:9]Ethyl azidoacetate (14.9 g, 115 mmol) was dissolved in tert-butanol (200 mL), and 95% 3-hydroxybenzonitrile (13.7 g, 110 mmol) was added. A solution of sodium ascorbate (2.18 g, 11 mmol) in water (100 mL) was added, followed by a 0.3 M solution of copper sulfate under argon. The mixture was stirred at room temperature for 12 hours. The solution was evaporated to dryness in vacuo, the residue was dissolved in EtOAc (100 mL), dried (MgSO4), filtered, evaporated in vacuo to give the title compound as brown crystals in ˜100% (27.7 g) yield.
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