(S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid → (S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid [1-(2-hydroxymethyl-phenyl)-1H-imidazol-4-yl]-amide

HRID 505060Notes

Reaction equation

HRID 505060 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][OH:16])[CH:8]=1)([O-])=O.[F:17][C:18]1[CH:19]=[C:20]([CH2:25][C:26]([NH:28][C@@H:29]([CH2:33][CH2:34][CH3:35])[C:30](O)=[O:31])=[O:27])[CH:21]=[C:22]([F:24])[CH:23]=1>>[OH:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:7]1[CH:8]=[C:4]([NH:1][C:30](=[O:31])[C@@H:29]([NH:28][C:26](=[O:27])[CH2:25][C:20]2[CH:21]=[C:22]([F:24])[CH:23]=[C:18]([F:17])[CH:19]=2)[CH2:33][CH2:34][CH3:35])[N:5]=[CH:6]1

Participants

3

Reactant 2

HCID 68463604(S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acidHCID 68464832(2-(4-nitro-1H-imidazol-1-yl)phenyl)methanol

Product 1

HCID 16113791(S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid [1-(2-hydroxymethyl-phenyl)-1H-imidazol-4-yl]-amide

Procedure

(2-(4-nitro-1H-imidazol-1-yl)phenyl)methanol was reduced and coupled with (S)-2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid (U.S. Ser. No. 11/078,898 filed Mar. 11, 2005) to afford the title compound: MS 443 m/z (M+1).

Sources & evidence

ORD record
ord-31e2c3b03bbb4e42b5bac369773e119e
Source dataset
uspto-grants-2010_08
Patent number
US07781435B2

Reaction notes

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