L-Valine → (S)-2-amino-1-((S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methylbutan-1-one

HRID 1873915Notes

Reaction equation

HRID 1873915 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3[C:18]([O:20]C(C)(C)C)=O)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:25][C@@H:26]([CH:30]([CH3:32])[CH3:31])C(O)=O>>[NH2:25][C@@H:26]([CH:30]([CH3:32])[CH3:31])[C:18]([N:14]1[CH2:15][CH2:16][CH2:17][C@H:13]1[C:11]1[NH:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:9][N:10]=1)=[O:20]

Participants

3

Reactant 2

HCID 6287L-ValineHCID 56605031(S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 57610942(S)-2-amino-1-((S)-2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methylbutan-1-one

Procedure

The title compound was prepared from (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate and (S)-2-amino-3-methylbutanoic acid by the procedures detailed in Examples 1 and 2. 1HNMR (300 MHz, DMSO-d6) δ 11.73 (s, 1H), 7.68 (d, J=5.9 Hz, 1H), 7.65 (d, J=5.9 Hz, 1H), 7.46-7.58 (m, 3H), 5.14, 5.05 (dd, J=7.0, 3.0 Hz, 1H, rotamers, 1:1 ratio), 3.66 (app t, J=6.5 Hz, 1H), 3.53-3.61 and 3.38-3.47 (m, 1H, rotamers, 1:1 ratio), 3.28 (s, 2H), 1.70-2.21 (m, 6H), 0.75-0.88 (m, 6H). LCMS: Anal. Calcd. for C18H23BrN4O: 390, 392. found: 391, 393 (M+H)+.

Sources & evidence

ORD record
ord-a700ade971f8482ab074856cfb330289
Source dataset
uspto-grants-2012_11
Patent number
US08303944B2

Reaction notes

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