Benzoylacetone → (2S)-2-{[(Z)-1-methyl-3-oxo-3-phenyl-1-propenyl]amino}-3-[4-(2-{5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl}ethoxy)phenyl]propanoic acid
Reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:32]([CH2:40][C:41](=O)[CH3:42])(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH3:42]/[C:41](/[NH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])=[CH:40]/[C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared (as described above for the preparation of Example 2) from 40 mg (0.092 mmol) of Intermediate 50 and 15 mg (0.092 mmol) of benzoylacetone to yield 32 mg of Example 7: TLC (DCM/MeOH, 4/1): Rf=0.48; 1H NMR (DMSO-d6, 300 MHz) δ11.49 (d, 1H, J=9.8), 8.17 (d, 2h, J=8.9), 7.9 (d, 2H, J=8.9), 7.85 (m, 2H), 7.44 (m, 3H), 7.19 (d, 2H, J=8.8), 6.89 (d, 2H, J=8.8), 5.60 (s, 1H), 4.23 (t, 2H, J=6.0), 4.16 (m, 1H), 3.21 (m, 2H), 2.99 (t, 2H, J=6.0), 2.82 (dd, 1H, J=14.2, 9.8), 2.42 (s, 3H), 1.78 (s, 3H); low resolution MS (ES+)m/e 579.0 (MH+).