[4-N-(3,4-dimethoxybenzyloxycarbonyl)-cytosin-1-yl]-acetic acid → N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[4-N-(3,4-dimethoxybenzyloxycarbonyl)-cytosin-1-yl]-acetyl}-glycine ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[CH3:2].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[CH2:28][O:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][N:36]([CH2:39][C:40](O)=[O:41])[C:35](=[O:43])[N:34]=1)=[O:31]>>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:12])=[O:11])[C:40](=[O:41])[CH2:39][N:36]1[CH:37]=[CH:38][C:33]([NH:32][C:30]([O:29][CH2:28][C:27]2[CH:44]=[CH:45][C:46]([O:47][CH3:48])=[C:25]([O:24][CH3:23])[CH:26]=2)=[O:31])=[N:34][C:35]1=[O:43])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound (5.31 g, 81%) was synthesized by the reaction of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (3.26 g, 9.5 mmol) and [4-N-(3,4-dimethoxybenzyloxycarbonyl)-cytosin-1-yl]-acetic acid (3.28 g, 9.03 mmol) as per the procedure of Example 20. 1H NMR (500 MHz; DMSO-d6) δ 10.72 (s, 1H), 8.27 (dd, 1H), 8.17 (dd, 1H), 7.90 (d, 0.6H), 7.82 (d, 0.4H), 7.69˜7.62 (m, 2H), 7.02 (s, 1H), 7.00 (t, 1H), 6.94 (s, 2H), 5.09 (s, 2H), 4.80 (s, 1.2H), 4.61 (s, 0.8H), 4.34 (s, 0.8H), 4.13 (q, 0.8H), 4.05 (s, 1.2H), 4.03 (q, 1.2H), 3.75 (s, 3H), 3.74 (s, 3H), 3.58 (t, 1.2H), 3.42-3.37 (m, 2H), 3.20 (t, 0.8H), 1.20 (t, 1.2H), 1.14 (t, 1.8H).
Sources & evidence
- ORD record
- ord-6296adec13f44d4cb35def3ede79b826
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07411065B2
Reaction notes
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