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

HRID 2300647Notes

Reaction equation

HRID 2300647 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].C(O)(C(F)(F)F)=O.[CH2:35]1[CH2:40][CH2:39][CH:38]([C:41](=[O:46])[CH2:42][C:43](=O)[CH3:44])[CH2:37][CH2:36]1>>[CH:38]1([C:41](=[O:46])/[CH:42]=[C:43](\[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])/[CH3:44])[CH2:39][CH2:40][CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 1620991-Cyclohexylbutane-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 70161424(2S)-2-{[(Z)-3-cyclohexyl-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 428 mg (0.89 mmol) of Intermediate 45 (as the TFA salt) and 150 mg (0.89 mmol) of Intermediate 33 to yield 245 mg (53% yield) of Example 43 as a solid beige-colored glass: TLC (DCM/MeOH (4:1): Rf=0.69; 1H NMR (DMSO-d6, 400 MHz) δ10.79 (d, 1H, J=9.0), 7.89 (m, 2H), 7.50-7.41 (m, 3H), 7.05 (d, 2H, J=8.4), 6.77 (d, 2H, J=8.4), 4.7 (s, 1H), 4.12 (t, 2H, J=6.5), 3.9 (br s, 1H), ), 3.04 (dd, 1H, J=13.6, 4.0), 2.87 (t, 2H, J=6.5), 2.64 (dd, 1H, J=13.6, 8.9), 2.32 (s, 3H), 1.9 (m, 1H), 1.6 (m, 4H), 1.5 (s, 3H), 1.25-1.05 (m, 4H): low resolution MS (ES+)m/e 517.3 (MH+).

Sources & evidence

ORD record
ord-4d43fe01a2c3486ab234790809113df4
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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