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-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoic acid

HRID 2300627Notes

Reaction equation

HRID 2300627 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]([F:28])=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:42])[CH2:37][C:38](=O)[CH2:39][CH3:40])=[CH:32][CH:31]=1>>[CH2:39](/[C:38](/[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]([F:28])=[CH:26][CH:27]=3)[O:19][C:20]=2[CH3:21])=[CH:11][CH:12]=1)[C:3]([OH:5])=[O:4])=[CH:37]/[C:36]([C:33]1[CH:32]=[CH:31][C:30]([F:29])=[CH:35][CH:34]=1)=[O:42])[CH3:40]

Participants

3

Reactant 2

HCID 125477611-(4-Fluorophenyl)pentane-1,3-dioneHCID 70159586(2S)-2-amino-3-(4-{2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoic acid

Product 1

HCID 9872523(2S)-2-{[(Z)-1-ethyl-3-(4-fluorophenyl)-3-oxo-1-propenyl]amino}-3-(4-{2-[2(4-fluorophenyl)-5-methyl-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 500 mg (1.56 mmol) of Intermediate 46 and 315 mg (1.56 mmol) of Intermediate 32 to yield 412 mg of Example 9: TLC (DCM/MeOH, 4/1): Rf=0.53; 1H NMR (DMSO-d6, 300 MHz) δ11.53 (d, 1H, J=9.3), 7.99 (m, 2H), 7.95 (m, 2H), 7.39 (t, 2H, J=8.7), 7.26 (t, 2H, J=8.7), 7.17 (d, 2H, J=8.1), 6.86 (d, 2H, J=8.1), 5.60 (s, 1H), 4.20 (t, 2H, J=6.6), 4.12 (m, 1H), 3.21 (m, 2H), 2.94 (t, 2H, J=6.6), 2.78 (dd, 1H, J=13.8, 8.4), 2.38 (s, 3H), 2.05 (m, 2H), 0.96 (t, 3H, J=7.5); low resolution MS (ES+)m/e 561.4 (MH+).

Sources & evidence

ORD record
ord-e8043551f7514b8592378a2f98a2698e
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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