Propionyl Acetophenone → (2S)-2-{[(Z)-1-ethyl-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]1([C:38](=[O:44])[CH2:39][C:40](=O)[CH2:41][CH3:42])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:41](/[C:40](/[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:39]/[C:38](=[O:44])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:42]Participants
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 17 mg (0.092 mmol) of Intermediate 16 to yield 21 mg of Example 5: TLC (DCM/MeOH, 4/1): Rf=0.50; 1H NMR (DMSO-d6, 400 MHz) δ11.59 (d, 1H, J=9.8), 8.09 (d, 2H, J=9.0), 7.85 (d, 2H, J=8.8), 7.78 (m, 2H), 7.39 (m, 3H), 7.12 (d, 2H, J=8.0), 6.80 (d, 2H, J=8.0), 5.54 (s, 1H), 4.15 (t, 2H, J=6.6), 4.17 (m, 1H), 3.11 (m, 1H), 2.90 (t, 2H, J=6.6), 2.72 (m, 1H), 2.33 (s, 3H), 1.98 (m, 2H), 0.9 (t, 3H, J=7.5); low resolution MS (ES+)m/e 593.1 (MH+).