(S)-2-Hydroxy-3-methylbutanoic acid → 2-(2-Hydroxy-3-methyl-butyrylamino)-pentanoic acid [1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-1H-imidazol-4-yl]-amide

HRID 553121Notes

Reaction equation

HRID 553121 reaction equation
[CH3:1][C:2]([N:11]1[CH:15]=[C:14]([NH:16][C:17](=[O:23])[CH:18]([NH2:22])[CH2:19][CH2:20][CH3:21])[N:13]=[CH:12]1)([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[OH:24][C@@H:25]([CH:29]([CH3:31])[CH3:30])[C:26](O)=[O:27]>>[CH3:1][C:2]([N:11]1[CH:15]=[C:14]([NH:16][C:17](=[O:23])[CH:18]([NH:22][C:26](=[O:27])[CH:25]([OH:24])[CH:29]([CH3:31])[CH3:30])[CH2:19][CH2:20][CH3:21])[N:13]=[CH:12]1)([CH3:10])[CH2:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 853180(S)-2-Hydroxy-3-methylbutanoic acidHCID 671643342-Amino-pentanoic acid [1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-1H-imidazol-4-yl]-amide

Product 1

HCID 115100932-(2-Hydroxy-3-methyl-butyrylamino)-pentanoic acid [1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-1H-imidazol-4-yl]-amide

Procedure

2-Amino-pentanoic acid [1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-1H-imidazol-4-yl]-amide was coupled with (S)-2-hydroxy-3-methyl-butyric acid to afford the title compound: 13C NMR (100 MHz, CDCl3) 13.9, 16.1, 19.1, 19.4, 25.9, 32.3, 35.4, 52.8, 55.5, 59.2, 67.4, 68.8, 105.3, 131.3, 137.2, 169.4, 174.1; MS m/z 424.4 (M+1).

Sources & evidence

ORD record
ord-e060b3d3d8f14285b08d4164ecf61ed5
Source dataset
uspto-grants-2011_05
Patent number
US07951958B2

Reaction notes

Loading…