1-(4-Fluorophenyl)pentane-1,3-dione → (2S)-2-{[(Z)-1-ethyl-3-(4-fluorophenyl)-3-oxo-1-propenyl]amino}-3-{4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}propanoic acid

HRID 2300643Notes

Reaction equation

HRID 2300643 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[CH:34]=[CH:33][C:32]([C:35](=[O:41])[CH2:36][C:37](=O)[CH2:38][CH3:39])=[CH:31][CH:30]=1>>[CH2:38](/[C:37](/[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])=[CH:36]/[C:35]([C:32]1[CH:31]=[CH:30][C:29]([F:28])=[CH:34][CH:33]=1)=[O:41])[CH3:39]

Participants

3

Reactant 2

HCID 125477611-(4-Fluorophenyl)pentane-1,3-dioneHCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 69836348(2S)-2-{[(Z)-1-ethyl-3-(4-fluorophenyl)-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 2) from 100 mg (0.27 mmol) of Intermediate 45 and 49 mg (0.27 mmol) of Intermediate 32 to yield 83 mg of Example 35: TLC (EtOAc/MeOH (7:3): Rf=0.28; 1H NMR (DMSO-d6, 400 MHz) δ11.38 (d, 1H, J=7.00), 7.84 (m. 4H), 7.45 (m, 3H), 7.16 (t, 2H, J=8.72), 7.09 (d, 2H, J=7.69), 6.77 (d, 2H, J=7.69), 5.49 (s, 1H), 4.11 (m, 2H), 4.01(m, br, 1H), 3.13 (m, 1H), 2.86 (m, 2H), 2.72 (s, br, 1H), 2.30 (s, 3H), 1.62 (s, 3H); low resolution MS (ES+) m/e 529 (MH+); RP-HPLC (Vydac C-18, 25 cm×4.6 mm; 30-100% CH3CN in H2O) with 0.1% HCO2H buffer: 30 minutes; 1 mL/min: tr=20.10 min (to=1.53).

Sources & evidence

ORD record
ord-775aea292f97449c8f7dd90e119077c1
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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