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

HRID 1714305Notes

Reaction equation

HRID 1714305 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:18])[CH:15]([NH2:17])[CH3:16])[N:10]=[CH:9]1)([CH3:7])[CH3:6].[OH:20][C@@H:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22](O)=[O:23]>>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:18])[CH:15]([NH:17][C:22](=[O:23])[CH:21]([OH:20])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:16])[N:10]=[CH:9]1)([CH3:7])[CH3:6]

Participants

3

Reactant 2

HCID 11097105(2S)-2-hydroxy-3,3-dimethylbutanoic acidHCID 671649443-[4-(2-Amino-propionylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester

Product 1

HCID 252063403-{4-[2-(2-Hydroxy-3,3-dimethyl-butyrylamino)-propionylamino]-imidazol-1-yl}-3-methyl-butyric acid methyl ester

Procedure

3-[4-(2-Amino-propionylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester was coupled with (S)-2-hydroxy-3,3-dimethyl-butyric acid to provide the title compound: C13 NMR (100 MHz, CDCl3) 19.2, 26.2, 28.1, 28.2, 35.2, 47.1, 48.6, 51.9, 56.4, 79.7, 105.1, 112.4, 131.0, 137.7, 169.7, 170.0, 173.0; MS 383.3 m/z (M+1).

Sources & evidence

ORD record
ord-9ffca09ce7584a06a5a07c1a94a570de
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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