(2S)-2-hydroxy-3,3-dimethylbutanoic acid → 2-{4-[2-(2-Hydroxy-3,3-dimethyl-butyrylamino)-pentanoylamino]-imidazol-1-yl}-2-methyl-propionic acid methyl ester

HRID 553110Notes

Reaction equation

HRID 553110 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].[OH:21][C@@H:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23](O)=[O:24]>>[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:23](=[O:24])[CH:22]([OH:21])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:15][CH2:16][CH3:17])[N:9]=[CH:8]1)([CH3:5])[CH3:6]

Participants

3

Reactant 2

HCID 11097105(2S)-2-hydroxy-3,3-dimethylbutanoic acidHCID 671654262-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-2-methyl-propionic acid methyl ester

Product 1

HCID 115240812-{4-[2-(2-Hydroxy-3,3-dimethyl-butyrylamino)-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 (S)-2-hydroxy-3,3-dimethyl-butyric acid to provide the title compound: C13 NMR (100 MHz, CDCl3) 13.9, 19.1, 26.1, 26.2, 26.3, 35.3, 35.5, 52.6, 53.3, 61.1, 79.6, 106.1, 131.9, 137.5, 169.6, 172.7, 173.1; MS 397.23 m/z (M+1).

Sources & evidence

ORD record
ord-c63dc27976114e6b9d5ce1e149688714
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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