Benzoyl chloride, 3-nitro- → HCID 54291431, compound

HRID 1018370Notes

Reaction equation

HRID 1018370 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>>[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]=1

Participants

3

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 726858benzyl (2S)-2-aminopropanoate

Product 1

HCID 54291431HCID 54291431, compound

Procedure

3-Nitrobenzoyl chloride was reacted with L-alanine benzyl ester, then reduced with aluminium amalgam to produce (S)-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), 7.95 (1H, m), 7.54 (1H, d), 7.40-7.35 (1H, m), 4.40 (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, 58.89; H, 8.28; N, 8.97%. C39H59N4O9.3.0 mols H2O requires: C, 58.85; H, 8.23; N, 8.86%.

Sources & evidence

ORD record
ord-6edb502377054c788fdb42de3b0a6329
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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