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

HRID 1392459Notes

Reaction equation

HRID 1392459 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-6be34dadbf594a1fb159a550f8431fc3
Source dataset
uspto-grants-2008_03
Patent number
US07342118B2

Reaction notes

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