2-(4-(((Benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid → N-{2-[5-(4-Chloro-2-nitrophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-N-{[4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetyl}-glycine Ethyl Ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])=[N:16][N:17]=1)(=[O:12])=[O:11])[CH3:2].[CH:29]([O:42][C:43]([NH:45][C:46]1[CH:51]=[CH:50][N:49]([CH2:52][C:53](O)=[O:54])[C:48](=[O:56])[N:47]=1)=[O:44])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])=[N:16][N:17]=1)(=[O:12])=[O:11])[C:53](=[O:54])[CH2:52][N:49]1[CH:50]=[CH:51][C:46]([NH:45][C:43]([O:42][CH:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:44])=[N:47][C:48]1=[O:56])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound was synthesized by the reaction of N-{2-[5-(4-chloro-2-nitrophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-glycine ethyl ester with [4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetic acid as per the procedure of example 13. 1H NMR (400 MHz; DMSO-d6) δ 10.97 (s, 1H), 9.16 (brs, 1H), 8.40 (d, 0.6H), 8.38 (d, 0.4H), 8.06–7.94 (m, 2H), 7.91 (d, 0.6H), 7.85 (d, 0.4H), 7.45 (d, 4H), 7.37 (t, 4H), 7.29 (t, 2H), 6.96–6.93 (m, 1H), 6.80 (s, 1H), 4.81 (s, 1.2H), 4.63 (s, 0.8H), 4.36 (s, 0.8H), 4.18 (q, 0.8H), 4.07 (s, 1.2H), 4.06 (q, 1.2H), 3.61 (t, 1.2H), 3.48–3.40 (m, 2H), 3.27 (t, 0.8H), 1.25 (t, 1.2H), 1.17 (t, 1.8H).
Sources & evidence
- ORD record
- ord-360661f7b1fc4782be38edab59a26e58
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211668B2
Reaction notes
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