[4-N-(2-methylthioethoxycarbonyl)-cytosin-1-yl]-acetic acid → N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[4-N-(2-methylthioethoxycarbonyl)-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][S:24][CH2:25][CH2:26][O:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][N:34]([CH2:37][C:38](O)=[O:39])[C:33](=[O:41])[N:32]=1)=[O:29]>>[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:38](=[O:39])[CH2:37][N:34]1[CH:35]=[CH:36][C:31]([NH:30][C:28]([O:27][CH2:26][CH2:25][S:24][CH3:23])=[O:29])=[N:32][C:33]1=[O:41])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound (2.60 g, 85%) was synthesized by the reaction of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol) and [4-N-(2-methylthioethoxycarbonyl)-cytosin-1-yl]-acetic acid (1.44 g, 5 mmol) as per the procedure of Example 20. 1H NMR (500 MHz; DMSO-d6) δ 8.89 (t, 0.6H), 8.75 (t, 0.4H), 8.28 (dd, 1H), 8.19 (dd, 1H), 7.90 (d, 0.6H), 7.84 (d, 0.4H), 7.67 (m, 2H), 6.99 (m, 1H), 4.81 (s, 1.2H), 4.62 (s, 0.8H), 4.35 (s, 0.8H), 4.26 (t, 2H), 4.14 (q, 0.8H), 4.06 (s, 1.2H), 4.04 (q, 1.2H), 3.59 (t, 1.2H), 3.42 (m, 2.0H), 3.21 (q, 0.8H), 2.73 (t, 2H), 2.12 (s, 3H), 1.20 (t, 1.2H), 1.15 (t, 1.8H).
Sources & evidence
- ORD record
- ord-7d03a688498c40508e7e5271dc17066b
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179896B2
Reaction notes
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