[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10](C=CC3C=CC=CC=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:21](O)(=O)[CH2:22][C:23]([CH2:28][C:29]([OH:31])=O)([C:25](O)=O)O.[C:34](O)(C)(C)[CH3:35].C[N+]1([O-])CC[O:43]CC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:29]([OH:31])[CH:28]([C:23]3[CH:22]=[CH:21][CH:35]=[CH:34][CH:25]=3)[OH:43])=[N:9]2)[CH:5]=[CH:6][CH:7]=12-(3-Chloro-phenyl)-5-styryl-2H-tetrazole (127.0 mg, 0.446 mmol) was weighed into a vial and citric acid (171.35 mg, 0.892 mmol) was added followed by a 1:1 mixture of t-butanol and water (3 mL). Potassium osmate oxide hydrate (0.3 mg) was added followed by 4-methyl morpholine N-oxide (in 1.5 mL of water) and the reaction was allowed to stir overnight. The reaction was filtered and washed with water and 1M hydrochloric acid to yield the title compound as a beige solid (95.4 mg, 68%). 1H NMR (MeOD) δ (ppm): 8.086 (s, 1H); 8.012 (d of t, 1H); 7.584 (m, 2H); 7.252 (m, 5H); 5.148 (s, 2H).
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