3-Nitrobenzoic acid → HCID 11769697, compound

HRID 1018366Notes

Reaction equation

HRID 1018366 reaction equation
[N+](C1C=C(C=CC=1)C(O)=O)([O-])=O.CCl.NCC(O)=O.[CH3:20][O:21][C:22](=[O:36])[CH2:23][NH:24][C:25](=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=1>>[CH3:20][O:21][C:22](=[O:36])[CH2:23][NH:24][C:25](=[O:35])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[CH:27]=1

Participants

4

Reactant 3

HCID 84973-Nitrobenzoic acidHCID 270962N-(2-Methoxy-2-oxoethyl)-3-nitrobenzene-1-carboximidic acidHCID 86743526HCID 86743526, compound

Product 1

HCID 11769697HCID 11769697, compound

Procedure

3-Nitro-benzoic acid was reacted with glycine methyl hydrochloride and the resulting (3-nitro-benzoylamino)-acetic acid methyl ester was hydrogenated to afford (3-amino-benzoylamino)-acetic acid methyl 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 methyl ester was hydrolysed using the same procedure as in Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 10.54 (1H, br s), 8.80 (1H, t), 8.25 (1H, s), 7.91 (1H, d), 7.61 (1H, d), 7.45 (1H, d), 3.92 (2H, m), 2.93 (3H, m), 1.98-1.33 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 57.22; H, 8.30; N, 8.81%. C38H57N5O9.4.0 mols H2O requires: C, 57.06; H, 8.19; N, 8.75%.

Sources & evidence

ORD record
ord-3fd0fd614c0049a5b89f5349fc52e5c2
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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