Benzoyl chloride, 3-nitro- → HCID 54291430, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)C(Cl)=O)([O-])=O.[CH2:13]([O:20][C:21](=[O:25])[C@@H:22]([CH3:24])N)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Sn](Cl)(Cl)(Cl)Cl>>[CH2:13]([O:20][C:21](=[O:25])[C@@H:22]([C:11]1[CH:10]=[CH:6][CH:5]=[C:4]([NH2:1])[CH:12]=1)[CH3:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Procedure
3-Nitrobenzoyl chloride was reacted with D-alanine benzyl ester, then reduced with tin chloride to produce (R)-2-(3-amino-phenyl)-propionic 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 hydrogenolysed using the same procedure as in Example 1, step e to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 11.96 (1H, br s), 9.46 (1H, br s), 8.57 (1H, br d), 8.16 (1H, s), 7.96 (1H, d), 7.54 (1H, d), 7.40-7.35 (1H, m), 4.41 (1H, m), 2.87 (2H, m), 2.63 (1H, m), 1.94-1.32 (30H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.15; H, 8.33; N, 9.04%. C39H59N5O9.2.0 mols H2O requires: C, 60.21; H, 8.16; N, 9.00%.
Sources & evidence
- ORD record
- ord-5be43ea6ee304ff9bbe7726609957bef
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
Loading…