1-(4-(Trifluoromethyl)phenyl)butane-1,3-dione → (2S)-3-(4-{2-[2-(4-isopropoxyphenyl)-5-methyl-1,3-oxazol4-yl]ethoxy}phenyl)-2-({(Z)-1-methyl-3-oxo-3-[4-(trifluoromethyl)phenyl]-1-propenyl}amino)propanoic acid

HRID 2300623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300623
[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]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[F:32][C:33]([F:47])([F:46])[C:34]1[CH:39]=[CH:38][C:37]([C:40](=[O:45])[CH2:41][C:42](=O)[CH3:43])=[CH:36][CH:35]=1>>[CH:29]([O:28][C:25]1[CH:24]=[CH:23][C:22]([C:18]2[O:19][C:20]([CH3:21])=[C:16]([CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:2]([NH:1]/[C:42](/[CH3:43])=[CH:41]\[C:40](=[O:45])[C:37]4[CH:38]=[CH:39][C:34]([C:33]([F:32])([F:46])[F:47])=[CH:35][CH:36]=4)[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=3)[N:17]=2)=[CH:27][CH:26]=1)([CH3:31])[CH3:30]

Komponenten

3

Edukt 2

HCID 166409101-(4-(Trifluoromethyl)phenyl)butane-1,3-dioneHCID 70160210(2S)-2-amino-3-(4-{2-[2-(4-isopropoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}phenyl)propanoic acid

Produkt 1

HCID 9960936(2S)-3-(4-{2-[2-(4-isopropoxyphenyl)-5-methyl-1,3-oxazol4-yl]ethoxy}phenyl)-2-({(Z)-1-methyl-3-oxo-3-[4-(trifluoromethyl)phenyl]-1-propenyl}amino)propanoic acid

Versuchsvorschrift

The title compound was prepared (as described above for the preparation of Example 2) from 75 mg (0.18 mmol) of Intermediate 51 and 41 mg (0.18 mmol) of Intermediate 24 to yield 48 mg (43% yield) of Example 3: TLC (DCM/MeOH, 4/1): Rf=0.42; 1H NMR (DMSO-d6, 400 MHz) δ11.5 (d, 1H, J=8.9), 7.95 (d, 2H, J=7.2), 7.77 (d, 2H, J=8.7), 7.72 (d, 2H, J=8.2), 7.1 (d, 2H, J=8.4), 6.97 (d, 2H, J=8.9), 6.79 (d, 2H, J=8.5), 5.58 (s, 1H), 4.65 (m, 1H), 4.11 (t, 2H, J=6.5), 4.1 (m, 1H), 3.16 (dd, 1H, J=13.7, 3.6), 2.84 (t, 2H, J=6.5), 2.74 (dd, 1H, 13.7, 9.0), 2.28 (s, 3H), 1.67 (s, 3H), 1.25 (d, 6H, J=6.0); low resolution MS (ES+)m/e 637.1 (MH+);

Quellen und Nachweise

ORD-Eintrag
ord-64b83de7815c4d0dae519a8e8075b005
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498174B1

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