1-(2-Fluoro-3-trifluoromethylphenyl)-1,3-pentanedione → (2S)-2-({(Z)-3-[2-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-3-oxo-1-propenyl}amino)-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}propanoic acid

HRID 2300638Notes

Reaction equation

HRID 2300638 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][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:28][C:29]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39](=[O:45])[CH2:40][C:41](=O)[CH2:42]C>>[F:28][C:29]1[C:34]([C:35]([F:37])([F:38])[F:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39](=[O:45])/[CH:40]=[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:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])/[CH3:42]

Participants

3

Reactant 2

HCID 179241921-(2-Fluoro-3-trifluoromethylphenyl)-1,3-pentanedioneHCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 69836245(2S)-2-({(Z)-3-[2-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-3-oxo-1-propenyl}amino)-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}propanoic acid

Procedure

The title compound was prepared (as described above for the preparation of Example 12) from 190 mg (0.52 mmol) of Intermediate 45 and 120 mg (0.52 mmol) of Intermediate 37 to yield 102 mg (35% yield) of Example 26: 1H NMR (DMSO-d6, 400 MHz) δ11.36 (d, 1H, J=8.9), 7.9 (m, 3H), 7.77 (t, 1H, J=6.9), 7.46 (m, 3H), 7.42 (m, 1H), 7.11 (d, 2H, J=8.5), 6.81 (d, 2H, J=8.5), 5.22 (s, 1H), 4.14 (t, 2H, J=6.6), 4.1 (m, 1H), 3.13 (m, 1H), 2.87 (t, 2H, J=6.6), 2.78 (dd, 1H, J=13.7, 8.5), 2.31 (s, 3H), 1.68 (s, 3H); low resolution MS (ES+)m e 597.4(MH+).

Sources & evidence

ORD record
ord-d02f962a63cb4d358c1dd7a7115c9f60
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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