3,5-Difluorophenylacetic acid → 3-(4-[2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino]-imidazol-1-yl)-3-methyl-butyric acid methyl ester

HRID 553103Notes

Reaction equation

HRID 553103 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:20])[CH:15]([NH2:19])[CH2:16][CH2:17][CH3:18])[N:10]=[CH:9]1)([CH3:7])[CH3:6].[F:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31](O)=[O:32])[CH:26]=[C:27]([F:29])[CH:28]=1>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:20])[CH:15]([NH:19][C:31](=[O:32])[CH2:30][C:25]2[CH:24]=[C:23]([F:22])[CH:28]=[C:27]([F:29])[CH:26]=2)[CH2:16][CH2:17][CH3:18])[N:10]=[CH:9]1)([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 671653603-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester

Product 1

HCID 116121213-(4-[2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino]-imidazol-1-yl)-3-methyl-butyric acid methyl ester

Procedure

3-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester was coupled with (3,5-Difluoro-phenyl)-acetic acid to provide the title compound: C13 NMR (100 MHz, CDCl3) 13.9, 19.0, 27.9, 28.1, 35.9, 42.7, 46.8, 51.8, 53.1, 56.3, 102.2, 102.5, 102.7, 105.1, 112.2, 112.3, 112.4, 112.5, 131.3, 137.9, 139.2, 161.8, 164.2, 164.3, 169.4, 169.9, 170.0; MS 451.2 m/z (M+1).

Sources & evidence

ORD record
ord-c65655e0929a47f2869c24239fc6e9aa
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

Loading…