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

HRID 2300644Notes

Reaction equation

HRID 2300644 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][CH:32]=[CH:31][C:30]=1[C:35](=[O:40])[CH2:36][C:37](=O)[CH3:38]>>[F:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](=[O:40])/[CH:36]=[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])/[CH3:38]

Participants

3

Reactant 2

HCID 151697841-(2-Fluorophenyl)butane-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 69836240(2S)-2-{[(Z)-3-(2-fluorophenyl)-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 2) from 100 mg (0.27 mmol) of Intermediate 45 and 58 mg (0.32 mmol) of Intermediate 20 to yield 55 mg of Example 37: TLC (EtOAc/MeOH (7:3): Rf=0.25; 1H NMR (DMSO-d6, 400 MHz) δ11.42 (d, 1H, J=8.93), 7.95 (m. 2H), 7.70 (dd, 1H, J=1.78, 7.69), 7.51 (m, 4H), 7.23 (m, 4H), 6.88 (d, 2H, J=8.50), 5.36 (s, 1H), 4.22 (m, 2H), 4.16 (brs, 1H), 3.18 (m, 1H), 2.94 (m, 2H), 2.84 (m, 1H), 2.40 (s, 3H), 1.70 (s, 3H); low resolution MS (ES−)m/e 545.1 (M-H); 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=19.47 min (to=1.43).

Sources & evidence

ORD record
ord-18a8279739154eb5bcae4dc41fe4a784
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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