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

HRID 2300634Notes

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.[C:35]1([C:41](=[O:47])[CH2:42][C:43](=O)[CH2:44][CH3:45])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:44](/[C:43](/[NH: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])=[CH:42]/[C:41](=[O:47])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:45]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 21408Propionyl Acetophenone

HCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 9958456(2S)-2-{[(Z)-1-ethyl-3-oxo-3-phenyl-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 1.03 g (2.1 mmol) of Intermediate 45 (as the TFA salt) and 740 mg (4.2 mmol) of Intermediate 16 to yield 500 mg of Example 20 as a white solid: TLC (EtOAc/MeOH, 7/3): Rf=0.35; 1H NMR (DMSO-d6, 400 MHz) δ11.55 (d, 1H, J=9.6), 7.93 (d, 2H, J=7.8), 7.84 (d, 2H, J=7.8), 7.57 (m, 3H), 7.52 (m, 3H), 7.18 (d, 2H, J=8.4), 6.87 (d, 2H, J=8.4), 5.58 (s, 1H), 4.21 (t, 2H, J=6.6), 4.16 (m, 1H), 3.21 (m, 1H), 2.95 (t, 2H, J=6.6), 2.80 (dd, 1H, J=13.5, 9.0), 2.42 (s, 3H), 2.08 (m, 2H), 1.04 (t, 3H, J=7.8); low resolution MS (ES+)m/e 525 (MH+).

Sources & evidence

ORD record: ord-f8d2b79230d0453d9ef85f4d13ff163e
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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