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

HRID 2300636Notes

Reaction equation

HRID 2300636 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].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:35](=[O:40])[CH2:36][C:37](=O)[CH3:38])=[CH:31][CH:30]=1>>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([C:35](=[O:40])/[CH:36]=[C:37](\[NH:1][C@@H:2]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]3[N:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:19][C:20]=3[CH3:21])=[CH:9][CH:8]=2)[C:3]([OH:5])=[O:4])/[CH3:38])=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 2380831-(4-Chlorophenyl)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 69835449(2S)-2-{[(Z)-3-(4-chlorophenyl)-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 54 mg (0.27 mmol) of Intermediate 28 to yield 76 mg of Example 24: TLC (DCM/MeOH (4:1): Rf=0.52; 1H NMR (DMSO-d6, 300 MHz) δ11.52 (d, 1H, J=9.6), 7.97 (m, 2H), 7.87 (d, 2H, J=8.6), 7.55 (m, 5H), 7.18 (d, 2H, J=8.5), 6.86 (d, 2H, J=8.5), 5.59 (s, 1H), 4.21 (t, 2H, J=6.1), 4.09 (m, 1H), 3.22 (m, 1H), 2.96 (t, 2H, J=6.1), 2.78 (dd, 1H, J=13.9, 9.4), 2.39 (s, 3H), 1.73 (s, 3H).

Sources & evidence

ORD record
ord-800176aa37fe4ddab4c2c5d715181432
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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