3-Nitrobenzenesulfonyl chloride → HCID 53668975, compound

HRID 1018365Notes

Reaction equation

[N+](C1C=C(S(Cl)(=O)=O)C=CC=1)([O-])=O.C(OC(=O)CN)C1C=CC=CC=1.[CH2:26]([O:33][C:34](=[O:49])[CH2:35][NH:36][S:37]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([N+:46]([O-])=O)[CH:41]=1)(=[O:39])=[O:38])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Sn](Cl)(Cl)(Cl)Cl>>[CH2:26]([O:33][C:34](=[O:49])[CH2:35][NH:36][S:37]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([NH2:46])[CH:41]=1)(=[O:39])=[O:38])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 4

HCID 84763-Nitrobenzenesulfonyl chloride

HCID 24287Tin tetrachloride

HCID 409140Benzyl glycinate

HCID 54182887HCID 54182887, compound

Product 1

HCID 53668975HCID 53668975, compound

Procedure

3-Nitro-benzenesulfonyl chloride was reacted with glycine benzyl ester and the resulting (3-nitro-benzensulfonylamino)-acetic acid benzyl ester was reduced with tin chloride to afford (3-amino-benzenesulfonylamino)-acetic acid benzyl ester. This was reacted with 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) according to the procedure of Example 20, step d. The benzyl ester was hydrolysed using the same procedure as in Example 1, step e to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.00 (1H, br s), 9.71 (1H, br s), 8.35 (1H, s), 7.96 (2H, m), 7.45 (2H, m), 3.57 (2H, s), 2.88 (2H, m), 2.60 (1H, m), 1.94-1.32 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 55.50; H, 7.88; N, 8.83%. C37H57N5O10.2.0 mols H2O requires: C, 55.55; H, 7.69; N, 8.75%.

Sources & evidence

ORD record: ord-01c82787189149f18e27f10d4135f24c
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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