Ethyl N-{2-[(1,3-benzothiazole-2-sulfonyl)amino]ethyl}glycinate → HCID 21868395, compound

HRID 349627Notes

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

Participants

Reactant 2

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

HCID 21868451HCID 21868451, compound

Product 1

HCID 21868395HCID 21868395, compoundYield 97.6%

Procedure

The title compound (6.28 g, 96%) was synthesized by the reaction of N-[2-(benzothiazole-2-sulfonylamino)-ethyl]-glycine ethyl ester (3.26 g, 9.5 mmol) and [6-N-(3,4-dimethoxybenzyloxycarbonyl)-adenin-9-yl]-acetic acid (3.50 g, 9.03 mmol) as per the procedure of Example 27. 1H NMR (500 MHz; DMSO-d6) 10.58 (s, 1H), 8.98 (brs, 0.6H), 8.77 (brs, 0.4H), 8.57 (s, 0.4H), 8.53 (s, 0.6H), 8.29 (d, 1H), 8.27 (m, 1H), 8.17 (d, 1H), 7.65 (m, 2H), 7.08 (s, 1H), 6.98 (d, 1H), 6.94 (d, 1H), 5.35 (s, 1.2H), 5.15 (s, 0.8H), 5.12 (s, 2H), 4.45 (s, 0.8H), 4.18 (q, 0.8H), 4.07 (s, 1.2H), 4.01 (q, 1.2H), 3.75 (s, 3H), 3.74 (s, 3H), 3.70 (t, 1.2H), 3.48 (t, 1.2H), 3.42 (t, 0.8H), 3.22 (t, 0.8H), 1.23 (t, 1.2H), 1.12 (t, 1.8H).

Sources & evidence

ORD record: ord-b0ad4404a1f8446394d848fa7c81054e
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179896B2

Reaction notes

Loading…