[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:18][OH:19].CCO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:11]([C:12](=[NH:13])[NH:18][OH:19])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]A 5 L round bottom flask equipped with an overhead stirrer, and 500 mL addition funnel was charged with 3-(t-butyloxycarbonylamino)benzonitrile (264.4 g, 1.21 mol), hydroxylamine hydrochloride (294.6 g, 4.24 mol) and 95% EtOH (1 L). The resulting suspension was treated with a solution of potassium carbonate (711.8 g, 5.15 mol) in water (1 L) and the suspension heated to 60° C. The reaction was followed by TLC and HPLC for starting material consumption to completion. The reaction mixture was then cooled to ambient temperature the organic layer was separated and concentrated to approximately 500 mL, then diluted with water (1 L). The resulting precipitate was collected by vacuum filtration and dried to yield the title compound as an off white solid.
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