HCID 18405518, compound → HCID 18405440, compound

HRID 1018358Notes

Reaction equation

HRID 1018358 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[C:24](O)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O:29][C:30](=[O:40])[CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=1)[CH3:32])C>>[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[N:15][C:14]=3[C:24]([NH:39][C:35]3[CH:34]=[C:33]([CH:31]([CH3:32])[C:30]([OH:40])=[O:29])[CH:38]=[CH:37][CH:36]=3)=[O:25])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

3

Reactant 2

HCID 18405518HCID 18405518, compoundHCID 54475761HCID 54475761, compound

Product 1

HCID 18405440HCID 18405440, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) was reacted with (±)-2-(3-amino-phenyl)-propionic acid ethyl ester (S. Mutti et al. Synth. Comm. 1997, 27, 425) 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) 12.20 (2H, br s), 9.44 (1H, s), 7.64 (2H, m), 7.23 (1H, m), 6.96 (1H, d), 3.61 (1H, m), 2.86 (2H, m), 2.60 (1H, m), 1.98-1.19 (30H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 62.88; H, 8.66; N, 7.68%. C38H58N4O8.1.5 mols H2O requires: C, 62.87; H, 8.47; N, 7.72%.

Sources & evidence

ORD record
ord-9d9b38c590ad46a79b2c8e638d3f05b4
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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