1-(4-Fluorophenyl)pentane-1,3-dione → (2S)-2-{[(Z)-1-ethyl-3-(4-fluorophenyl)-3-oxo-1-propenyl]amino}-3-(4-{2-[2-(4-isopropoxyphenyl)-5-methyl-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]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:45])[CH2:40][C:41](=O)[CH2:42][CH3:43])=[CH:35][CH:34]=1>>[CH2:42](/[C:41](/[NH:1][C@@H:2]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[CH:11][CH:12]=1)[C:3]([OH:5])=[O:4])=[CH:40]/[C:39]([C:36]1[CH:35]=[CH:34][C:33]([F:32])=[CH:38][CH:37]=1)=[O:45])[CH3:43]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared (as described above for the preparation of Example 2) from 75 mg (0.177 mmol) of Intermediate 51 and 39 mg (0.194 mmol) of Intermediate 32 to yield 70 mg of Example 15: TLC (DCM/MeOH (4:1): Rf=0.55; 1H NMR (DMSO-d6, 300 MHz) δ11.53 (d, 1H, J=9.6), 7.89 (dd, 2H, J=8.8, 5.7), 7.85 (d, 2H, J=8.8), 7.26 (t, 2H, J=8.8), 7.18 (d, 2H, J=8.5), 7.05 (d, 2H, J=8.8), 6.86 (d, 2H, J=8.5), 5.60 (s, 1H), 4.73 (hept, 1H, J=6.0), 4.19 (t, 2H, J=6.7), 4.13 (br s, 1H), 3.19 (m, 1H), 2.92 (t, 2H, J=6.6), 2.80 (dd, 1H, J=14.0, 9.2), 2.36 (s, 3H), 2.07 (m, 2H), 1.34 (d, 6H, J=6.0), 0.99 (t, 3H, J=7.5); low resolution MS (ES+)m/e 601.1 (MH+).
Sources & evidence
- ORD record
- ord-9d79b74067484d65b8803cff42571f0a
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498174B1
Reaction notes
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