3-(4-Aminophenyl)propionic acid → HCID 18405655, compound

HRID 1018378Notes

Reaction equation

HRID 1018378 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:13]12([CH2:23][CH2:24][C:25]3[NH:29][C:28]([CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[N:27][C:26]=3[C:36](O)=[O:37])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>>[C:13]12([CH2:23][CH2:24][C:25]3[NH:29][C:28]([CH:30]4[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)=[N:27][C:26]=3[C:36]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=3)=[O:37])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2

Participants

3

Reactant 2

HCID 754513-(4-Aminophenyl)propionic acidHCID 18405518HCID 18405518, compound

Product 1

HCID 18405655HCID 18405655, compound

Procedure

3-(4-Amino-phenyl)-propionic acid acid benzyl ester (prepared in two steps from 4-nitrocinnamic acid) 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) 12.00 (1H, br s), 9.28 (1H, br s), 7.63 (1H, d), 7.14 (1H, d), 2.86 (2H, m), 2.76 (2H, t), 2.64 (1H, m), 2.62 (2H, m), 2.49 (2H, m), 1.93-1.30 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.77; H, 8.69; N, 7.49%; C38H58N4O8.3.0 H2O requires: C, 60.62; H, 8.57; N, 7.44%.

Sources & evidence

ORD record
ord-c82849317c72415e85cbd46dc9123f16
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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