3,5-Difluoromandelic acid → 2-(4-{2-[2-(3,5-Difluoro-phenyl)-2-hydroxy-acetylamino]-pentanoylamino}-imidazol-1-yl)-2-methyl-propionic acid methyl ester

HRID 1714301Notes

Reaction equation

HRID 1714301 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([N:7]1[CH:11]=[C:10]([NH:12][C:13](=[O:19])[CH:14]([NH2:18])[CH2:15][CH2:16][CH3:17])[N:9]=[CH:8]1)([CH3:6])[CH3:5].[F:21][C:22]1[CH:23]=[C:24]([CH:29]([OH:33])[C:30](O)=[O:31])[CH:25]=[C:26]([F:28])[CH:27]=1>>[CH3:1][O:2][C:3](=[O:20])[C:4]([N:7]1[CH:11]=[C:10]([NH:12][C:13](=[O:19])[CH:14]([NH:18][C:30](=[O:31])[CH:29]([C:24]2[CH:25]=[C:26]([F:28])[CH:27]=[C:22]([F:21])[CH:23]=2)[OH:33])[CH2:15][CH2:16][CH3:17])[N:9]=[CH:8]1)([CH3:5])[CH3:6]

Participants

3

Reactant 2

HCID 5886483,5-Difluoromandelic acidHCID 671654262-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-2-methyl-propionic acid methyl ester

Product 1

HCID 117051102-(4-{2-[2-(3,5-Difluoro-phenyl)-2-hydroxy-acetylamino]-pentanoylamino}-imidazol-1-yl)-2-methyl-propionic acid methyl ester

Procedure

2-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-2-methyl-propionic acid methyl ester was coupled with (3,5-Difluoro-phenyl)-hydroxy-acetic acid to provide the title compound: C13 NMR (100 MHz, CDCl3) 13.7, 13.8, 19.0, 19.1, 26.0, 35.3, 35.7, 53.0, 53.2, 53.3, 61.2, 61.3, 73.3, 73.4, 103.5, 103.7, 106.1, 106.3, 109.6, 109.8, 110.1, 131.6, 131.8, 137.0, 137.1, 144.0, 161.9, 164.3, 169.3, 169.6, 171.9, 172.0, 172.5; MS 453.20 m/z (M+1).

Sources & evidence

ORD record
ord-7970985f2100473fb22d86c5755730e4
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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