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

HRID 553104Notes

Reaction equation

HRID 553104 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:20])[CH:15]([NH2:19])[CH2:16][CH2:17][CH3:18])[N:10]=[CH:9]1)([CH3:7])[CH3:6].[OH:22][C@@H:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24](O)=[O:25]>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:20])[CH:15]([NH:19][C:24](=[O:25])[CH:23]([OH:22])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:16][CH2:17][CH3:18])[N:10]=[CH:9]1)([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 11097105(2S)-2-hydroxy-3,3-dimethylbutanoic acidHCID 671653603-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester

Product 1

HCID 115751203-{4-[2-(2-Hydroxy-3,3-dimethyl-butyrylamino)-pentanoylamino]-imidazol-1-yl}-3-methyl-butyric acid methyl ester

Procedure

3-[4-(2-Amino-pentanoylamino)-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) 13.9, 19.1, 26.3, 28.1, 35.2, 35.3, 47.1, 51.9, 52.7, 56.4, 79.9, 105.0, 131.0, 137.6, 169.3, 170.1, 173.1; MS m/z 411.1 (M+1).

Sources & evidence

ORD record
ord-dfe9177004ae489b887ff6c880379905
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

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