Ethyl N-{2-[(1,3-benzothiazole-2-sulfonyl)amino]ethyl}glycinate → HCID 136364038, compound

HRID 349632Notes

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:47]=[CH:48][C:49]=1[O:50][CH3:51])[CH2:28][O:29][C:30]([NH:32][C:33]1[NH:34][C:35](=[O:46])[C:36]2[N:37]=[CH:38][N:39]([CH2:42][C:43](O)=[O:44])[C:40]=2[N:41]=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:43](=[O:44])[CH2:42][N:39]1[CH:38]=[N:37][C:36]2[C:35](=[O:46])[NH:34][C:33]([NH:32][C:30]([O:29][CH2:28][C:27]3[CH:47]=[CH:48][C:49]([O:50][CH3:51])=[C:25]([O:24][CH3:23])[CH:26]=3)=[O:31])=[N:41][C:40]1=2)[CH3:2]

Participants

Reactant 2

HCID 21868443Ethyl N-{2-[(1,3-benzothiazole-2-sulfonyl)amino]ethyl}glycinate

HCID 136364015HCID 136364015, compound

Product 1

HCID 136364038HCID 136364038, compoundYield 68.1%

Procedure

The title compound (2.48 g, 68%) was synthesized by the reaction of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (1.72 g, 5 mmol) and [2-N-(3,4-dimethoxybenzyloxycarbonyl)-guanin-9-yl]-acetic acid (2.02 g, 5 mmol) as per the procedure of Example 20. 1H NMR (500 MHz; DMSO-d6) δ 8.26 (dd, 1H), 8.14 (dd, 1H), 7.80 (s, 0.6H), 7.76 (s, 0.4H), 7.65 (m, 2H), 7.04 (s, 1H), 6.95 (m, 2H), 5.15 (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), 3.74 (s, 3H), 3.73 (s, 3H), 3.62 (t, 1.2H), 3.43 (t, 1.2H), 3.39 (t, 0.8H), 3.20 (t, 0.8H), 1.21 (t, 1.2H), 1.13 (t, 1.8H).

Sources & evidence

ORD record: ord-7c5721c3f2f340a3a25a929d6edb0ea6
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179896B2

Reaction notes

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