(4-[2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino]-imidazol-1-yl)-acetic acid methyl ester → 2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid [1-(2-hydroxy-ethyl)-1H-imidazol-4-yl]-amide

HRID 1714360Notes

Reaction equation

HRID 1714360 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:28])[CH:12]([NH:16][C:17](=[O:27])[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH2:13][CH2:14][CH3:15])[N:7]=[CH:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[OH:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:28])[CH:12]([NH:16][C:17](=[O:27])[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH2:13][CH2:14][CH3:15])[N:7]=[CH:6]1

Participants

3

Reactant 2

HCID 11582250(4-[2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino]-imidazol-1-yl)-acetic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 115960342-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoic acid [1-(2-hydroxy-ethyl)-1H-imidazol-4-yl]-amide

Procedure

(4-{2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino}-imidazol-1-yl)-acetic acid methyl ester was reduced using LAH to afford the title compound: C13 NMR (100 MHz, CDCl3) 12.8, 19.0, 34.3, 41.6, 49.8, 53.6, 61.1, 101.6, 101.8, 102.1, 108.4, 111.9, 112.1, 112.1, 134.0, 136.6, 162.0, 164.5, 170.3, 171.4; MS m/z 381.1 (M+1).

Sources & evidence

ORD record
ord-0f5bb0419f0b4c1b8c4ead25914e4416
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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