Nitric Acid → (+/-)-5'-Amino-6'-nitro-3-methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione
반응식
[CH3:1][N:2]1[C:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=3)[CH2:7]2)[C:5](=[O:18])[NH:4][C:3]1=[O:19].[N+:20]([O-])(O)=O.OS(O)(=O)=O>>[NH2:20][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][C:11]=1[N+:15]([O-:17])=[O:16])[CH2:14][C:6]1([C:5](=[O:18])[NH:4][C:3](=[O:19])[N:2]1[CH3:1])[CH2:7]2참가 물질
4
실험 절차
To (±)-5′-amino-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (100 mg, 0.432 mmol, described in Intermediate 7) at 0° C. were added 70% HNO3 (1 mL) followed by conc. H2SO4 (1 mL). The resulting mixture was allowed to warm to ambient temperature and stirred for 18 h, then poured onto ice and the precipitate was removed by filtration. The aqueous filtrate was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=277 (M+1).