[4-N-(3,4-dimethoxybenzyloxycarbonyl)-cytosin-1-yl]-acetic acid → 1-(Benzothiazole-2-sulfonyl)-4-{[4-N-(3,4-dimethoxybenzyloxycarbonyl)-cytosin-1-yl]-acetyl}-piperazin-2-one
Reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26])(=[O:19])=[O:18].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:48]=[CH:49][C:50]=1[O:51][CH3:52])[CH2:32][O:33][C:34]([NH:36][C:37]1[CH:42]=[CH:41][N:40]([CH2:43][C:44](O)=[O:45])[C:39](=[O:47])[N:38]=1)=[O:35]>>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:44](=[O:45])[CH2:43][N:40]2[CH:41]=[CH:42][C:37]([NH:36][C:34]([O:33][CH2:32][C:31]3[CH:48]=[CH:49][C:50]([O:51][CH3:52])=[C:29]([O:28][CH3:27])[CH:30]=3)=[O:35])=[N:38][C:39]2=[O:47])[CH2:22][C:21]1=[O:26])(=[O:19])=[O:18]Participants
3
Procedure
The title compound was synthesized by the reaction of 1-(benzothiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt with [4-N-(3,4-dimethoxybenzyloxycarbonyl)-cytosin-1-yl]-acetic acid as per the procedure of Example 52. 1H NMR (500 MHz; DMSO-d6) δ 10.73 (brs, 1H), 8.34 (m, 1H), 8.26 (m, 1H), 7.90 (d, 0.6H), 7.84 (d, 0.4H), 7.71 (m, 2H), 7.03 (s, 1H), 7.02 (t, 1H), 6.94 (s, 2H), 5.09 (s, 2H), 4.82 (s, 1.2H), 4.72 (s, 0.8H), 4.45 (s, 0.8H), 4.27 (s, 1.2H), 4.21 (t, 1.2H), 4.06 (t, 0.8H), 3.99 (t, 1.2H), 3.85 (t, 0.8H), 3.75 (s, 3H), 3.74 (s, 3H).
Sources & evidence
- ORD record
- ord-2b2f9364ea1c4233af95c5dd7c62bbcc
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07411065B2
Reaction notes
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