Benzyl Bromide → N-[2-(1-(triphenylmethyl)imidazol-4-yl)ethyl]-N'-tert-butoxycarbonyl-N'-phenylmethyl-sulfamide
Reaction equation
NCCC1N=CN([C:9](C2C=CC=CC=2)(C2C=CC=CC=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)C=1.[C:28]1([C:34]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[N:35]2[CH:39]=[C:38]([CH2:40][CH2:41][NH:42][S:43]([NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])(=[O:45])=[O:44])[N:37]=[CH:36]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(Br)C1C=CC=CC=1>>[C:60]1([C:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[N:35]2[CH:39]=[C:38]([CH2:40][CH2:41][NH:42][S:43]([N:46]([C:47]([O:49][C:50]([CH3:53])([CH3:51])[CH3:52])=[O:48])[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:45])=[O:44])[N:37]=[CH:36]2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1Participants
Procedure
4-(2-Aminoethyl)-1-(triphenylmethyl)-imidazole (Example 17 step b) was converted to N-2-[1-(triphenylmethyl)imidazol-4-yl]ethyl-N'-tert-butoxycarbonyl-sulfamide according to the procedure of Example 12 step a. The subsequent alkylation with benzyl bromide was performed essentially as Example 12 step b and gave N-[2-(1-(triphenylmethyl)imidazol-4-yl)ethyl]-N'-tert-butoxycarbonyl-N'-phenylmethyl-sulfamide. The final deprotection was carried out in the manner of Example 17 step b and the title compound (Rf 0.21; 1:10:90 ammonia(880)/methanol/dichloromethane) was isolated as a colourless oil: 1H NMR (300 Hz, d6 -DMSO) 7.50(1H, s), 7.30(6H, m), 6.95(1H, t), 6.78(1H, s), 3.96(2H, s), 3.03(2H, dd), 2.65(2H, t). The maleate salt was prepared by lyophilysis of an equimolar solution of the product and maleic acid in water/dioxan. Found: C 48.05, H 5.10, N 13.87%; C16H2ON4O6S requires: C 48.48, H 5.09 N 14.13%.
Sources & evidence
- ORD record
- ord-8be5c73440c14589aa48975d1543715a
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080871
Reaction notes
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