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 2300623Notes

Reaction equation

HRID 2300623 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]([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]

Participants

3

Reactant 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

Product 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

Procedure

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+);

Sources & evidence

ORD record
ord-64b83de7815c4d0dae519a8e8075b005
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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