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

HRID 2300635Notes

Reaction equation

HRID 2300635 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:49])[CH2:42][C:43](=O)[CH2:44][CH2:45][CH2:46][CH3:47])[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:49])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:45][CH2:46][CH3:47]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4365851-(Phenyl)-1,3-heptanedioneHCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 9872325(2S)-2-{[(Z)-1-butyl-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 1.0 g (2.05 mmol) of Intermediate 45 (as the TFA salt) and 0.86 g (4.2 mmol) of Intermediate 18 to yield 290 mg (25% yield) of Example 23 as a solid: TLC (EtOAc/MeOH , 7/3): Rf=0.55; 1H NMR (DMSO-d6, 400 MHz) δ11.59 (d, 1H, J=9.7), 7.86 (m, 2H), 7.76 (m, 2H), 7.48-7.34 (m, 6H), 7.10 (d, 2H, J=8.5), 7.10 (t, 2H, J=8.4), 6.8 (d, 2H, J=8.6), 5.52 (s, 1H), 4.12 (t, 2H, J=6.5), 4.02 (m, 1H), 3.16 (m, 1H), 2.86 (t, 2H, J=6.5), 2.75 (dd, 1H, J=13.5, 9.5), 2.31 (s, 3H), 1.9 (m, 2H), 1.3-1.1 (m, 4H), 0.73 (t, 3H, J=6.9); low resolution MS (ES+)m/e 553.2 (MH+).

Sources & evidence

ORD record
ord-f5b56fd2d9d24c3e9af6503c9f259d66
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

Loading…