[CH3:1]/[CH:2]=[C:3]1/[CH2:4][CH:5]2[N:16]([CH2:17]/1)[C:14](=[O:15])[C:13]1[C:8](=[CH:9][C:10]([OH:20])=[C:11]([O:18][CH3:19])[CH:12]=1)[N:7]=[CH:6]2.[C:21](=[O:24])([O-])[O-].[K+].[K+].[C:27]([O:31][C:32]([NH:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[C:43]([CH2:45][O:46]S(C2C=CC(C)=CC=2)(=O)=O)[N:42]=[C:41]([CH2:57]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:40]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O.[I-].[K+]>[C:27]([O:31][C:32]([NH:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:40]=[C:41]([CH2:57][O:20][C:10]2[C:11]([O:18][CH3:19])=[CH:12][C:13]3[C:14](=[O:15])[N:16]4[CH2:17][C:3](=[CH:2][CH3:1])[CH2:4][C@H:5]4[CH:6]=[N:7][C:8]=3[CH:9]=2)[N:42]=[C:43]([CH2:45][O:46][C:10]2[C:11]([O:24][CH3:21])=[CH:12][C:13]3[C:14](=[O:15])[N:16]4[CH2:17][C:3](=[CH:2][CH3:1])[CH2:4][C@H:5]4[CH:6]=[N:7][C:8]=3[CH:9]=2)[CH:44]=1)=[O:33])([CH3:28])([CH3:29])[CH3:30]To a stirred solution of pre-tomaymycin (30 mg) in dimethylformamide (0.5 mL), were added potassium carbonate (45.7 mg), a solution of 4-(3-tert-butoxycarbonylamino-propoxy)-2,6-bis-(tosyloxymethyl)-pyridine (41 mg) in dimethylformamide (0.5 mL) and potassium iodide (18.3 mg). The reaction was stirred for 20 h at 30° C. Solids were filtered off and washed with dimethylformamide (0.2 mL). Water (0.5 mL) was added to the combined dimethylformamide solution and formic acid was added until complete dissolution of the precipitate. The resulting solution was injected for HPLC purification according to method B1. The appropriate fractions were combined and concentrated by centrifugal evaporation over a Jouan Model RC10.10. apparatus to afford 8,8′-[4-(3-tert-butoxycarbonylaminopropyloxy)-2,6-pyridine-diylbis(methylenoxy)]-bis[(S)-2-eth-(E)-ylidene-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one] (8.3 mg).
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