Benzoyl chloride, 3-nitro- → HCID 53828089, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)C(Cl)=O)([O-])=O.Cl.[C:14]([O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1)([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=1)=[O:25])([CH3:17])([CH3:15])[CH3:16]Participants
Procedure
3-Nitrobenzoyl chloride was reacted with L-proline tert-butyl ester hydrochloride, then hydrogenated to produce (S)-1-(3-amino-phenyl)-pyrrolidin-2-carboxylic acid tert-butyl 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 tert-butyl ester was deprotected by treating the chloroform solution of the ester with 4.0 M solution of hydrogen chloride in dioxan to afford the title compound as the hydrochloride salt. 1H NMR (300 MHz, d6-DMSO) (mixture of tautomers) 14.10 (1H, br s), 10.95 (1H, br m), 8.00 and 7.79 (1H, 2×m), 7.88 (1H, m), 7.41 (1H, m), 7.26 and 7.11 (1H, 2×), 4.43 (1H, m), 4.12 (1H, m), 3.48 (1H,m), 2.97 (3H, m), 2.28-1.29 (31H, m). Found: C, 64.88; H, 7.78; N, 8.92%; C34H45ClN4O4.1.0 mol H2O requires: C, 65.11; H, 7.55; N, 8.93%.
Sources & evidence
- ORD record
- ord-dec0f56db94f4e4a93b3ab7c1ee5c2ec
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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