Ethyl 2-((2-(benzo[d]thiazole-2-sulfonamido)ethyl)amino)acetate → N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-{[2-N-(4-methoxybenzyloxycarbonyl)-guanin-9-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:49]=[CH:48][C:28]([CH2:29][O:30][C:31]([NH:33][C:34]2[NH:35][C:36](=[O:47])[C:37]3[N:38]=[CH:39][N:40]([CH2:43][C:44](O)=[O:45])[C:41]=3[N:42]=2)=[O:32])=[CH:27][CH:26]=1>>[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:44](=[O:45])[CH2:43][N:40]1[CH:39]=[N:38][C:37]2[C:36](=[O:47])[NH:35][C:34]([NH:33][C:31]([O:30][CH2:29][C:28]3[CH:48]=[CH:49][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)=[O:32])=[N:42][C:41]1=2)[CH3:2]Participants
3
Procedure
The title compound (2.72 g, 78%) was synthesized by the reaction of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol) and [2-N-(4-methoxybenzyloxycarbonyl)-guanin-9-yl]-acetic acid (1.89 g, 5 mmol) as per the procedure of Example 20. 1H NMR (500 MHz; DMSO-d6) δ 8.26 (dd, 1H), 8.15 (dd, 1H), 7.80 (s, 0.6H), 7.76 (s, 0.4H), 7.65 (m, 2H), 7.36 (d, 2H), 6.94 (d, 2H), 5.16 (s, 2H), 5.09 (s, 1.2H), 4.90 (s, 0.8H), 4.42 (s, 0.8H), 4.16 (q, 0.8H), 4.06 (s, 1.2H), 4.03 (q, 1.2H), 3.75 (s, 3H), 3.63(t, 1.2H), 3.43 (t, 1.2H), 3.39 (t, 0.8H), 3.20 (t, 0.8H), 1.21 (t, 1.2H), 1.12 (t, 1.8H).
Sources & evidence
- ORD record
- ord-374402ab1a604af9a0317fd731c0468d
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371860B2
Reaction notes
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