3,5-Difluoromandelic acid → 2-[2-(3,5-Difluoro-phenyl)-2-hydroxy-acetylamino]-pentanoic acid [1-(1-ethyl-propyl)-1H-imidazol-4-yl]-amide

HRID 1714308Notes

Reaction equation

HRID 1714308 reaction equation
[CH2:1]([CH:3]([N:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:18])[CH:13]([NH2:17])[CH2:14][CH2:15][CH3:16])[N:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2].[F:19][C:20]1[CH:21]=[C:22]([CH:27]([OH:31])[C:28](O)=[O:29])[CH:23]=[C:24]([F:26])[CH:25]=1>>[CH2:1]([CH:3]([N:6]1[CH:10]=[C:9]([NH:11][C:12](=[O:18])[CH:13]([NH:17][C:28](=[O:29])[CH:27]([C:22]2[CH:23]=[C:24]([F:26])[CH:25]=[C:20]([F:19])[CH:21]=2)[OH:31])[CH2:14][CH2:15][CH3:16])[N:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

3

Reactant 2

HCID 5886483,5-Difluoromandelic acidHCID 671650412-Amino-pentanoic acid [1-(1-ethyl-propyl)-1H-imidazol-4-yl]-amide

Product 1

HCID 115969792-[2-(3,5-Difluoro-phenyl)-2-hydroxy-acetylamino]-pentanoic acid [1-(1-ethyl-propyl)-1H-imidazol-4-yl]-amide

Procedure

2-Amino-pentanoic acid [1-(1-ethyl-propyl)-1H-imidazol-4-yl]-amide was coupled with (3,5-Difluoro-phenyl)-hydroxy-acetic acid to afford the title compound: C13 NMR (100 MHz, CDCl3) 10.7, 13.7, 13.7, 19.0, 19.1, 35.5, 35.7, 52.9, 53.2, 62.9, 73.4, 73.5, 103.4, 103.7, 105.0, 105.2, 109.6, 109.8, 109.9, 110.1, 132.5, 132.6, 137.4, 137.5, 144.1, 161.7, 161.9, 164.3, 169.2, 169.6, 171.8, 172.0; MS 423.21 m/z (M+1); Diastereomers separated using Chiralpak AD column, elute 50:50 heptane:ethanol; Flow Rate 275 mL/min.

Sources & evidence

ORD record
ord-bf29ff7385ea4d1c8c726b28c748edc5
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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