tert-Butyl 3-(3-aminophenyl)propanoate → 3-(3-{[5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-phenyl)-propionic acid tert-butyl ester

HRID 1018324Notes

Reaction equation

HRID 1018324 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])=[N:15][C:14]=3[C:25](O)=[O:26])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:28]([O:32][C:33](=[O:43])[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([NH2:42])[CH:37]=1)([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33](=[O:43])[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([NH:42][C:25]([C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)=[O:26])[CH:37]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 16731538tert-Butyl 3-(3-aminophenyl)propanoateHCID 184053605-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 572222493-(3-{[5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carbonyl]-amino}-phenyl)-propionic acid tert-butyl esterYield 63.2%

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid (Example 93) (364 mg, 1.00 mmol) was reacted with 3-(3-amino-phenyl)-propionic acid tert-butyl ester (243 mg, 1.10 mmol) according to the procedure of Example 70, step c to afford the product as a colourless foam (359 mg, 63%). 1H NMR (300 MHz, CDCl3) 9.14 (1H, br s), 9.07 (1H, br s), 7.59-7.51 (3H, m), 7.35-7.22 (4H, m), 6.94 (1H, d), 3.16 (2H, m), 2.92 (2H, m), 2.60 (3H, s), 2.56 (2H, m), 1.99 (3H, s), 1.76-1.44 (23H, m).

Sources & evidence

ORD record
ord-14d3d89d42884319a0c9cbd7a8056048
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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