C([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14]1)[CH2:8][CH2:7]2)(O)=O.[N-:20]=[N+]=[N-].[Na+].[OH-].[Na+]>OS(O)(=O)=O>[NH2:20][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][C:9]1([C:17](=[O:18])[NH:16][C:15](=[O:19])[NH:14]1)[CH2:8][CH2:7]2A stirred mixture of (±)-6′-carboxy-3′,4′-dihydro-1′H-spiro[imidazolidine-4,2′-naphthalene]-2,5-dione (described in Intermediate 1) (1.50 g, 5.76 mmol), and sodium azide (749 mg, 11.53 mmol) in conc. H2SO4 (30 mL) was heated to 50° C. for 2 h, then allowed to cool to ambient temperature. The mixture was adjusted to pH 8 by addition of 6 N aqueous NaOH and concentrated in vacuo to precipitate a solid. The precipitate was collected by filtration and washed extensively with H2O. Drying in vacuo afforded the title compound. MS: m/z=232 (M+1).
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