3-Nitrobenzoic acid → HCID 54968862, compound
Reaction equation
[N+](C1C=C(C=CC=1)C(O)=O)([O-])=O.C(Cl)C.N(CC(O)=O)C.[CH2:22]([O:24][C:25](=[O:40])[CH2:26][N:27]([C:29](=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-])=O)[CH:31]=1)[CH3:28])[CH3:23]>>[CH2:22]([O:24][C:25](=[O:40])[CH2:26][N:27]([C:29](=[O:39])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH2:36])[CH:31]=1)[CH3:28])[CH3:23]Participants
Procedure
3-Nitro-benzoic acid was reacted with sarcosine ethyl hydrochloride and the resulting [(3-nitro-benzoyl)-methyl-amino]-acetic acid ethyl ester was hydrogenated to afford [(3-amino-benzoyl)-methyl-amino]-acetic acid ethyl 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 ethyl ester was hydrolysed using the same procedure as in Example 247, step b to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 10.79 (1H, br s), 7.83 (2H, m), 7.44 (1H, m), 7.14 and 7.01 (1H, 2×m), 4.15 and 3.97 (2H, 2×s), 2.94 (6H, m), 2.03-1.25 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.14; H, 8.24; N, 8.97%. C39H59N5O9.2.0 mols H2O requires: C, 60.21; H, 8.16, N 9.00%.
Sources & evidence
- ORD record
- ord-b01466857a6d42dba660c0b14ca10471
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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