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

HRID 2300639Notes

Reaction equation

HRID 2300639 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.[CH:35]([O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45](=[O:50])[CH2:46][C:47](=O)[CH3:48])=[CH:41][CH:40]=1)([CH3:37])[CH3:36]>>[CH:35]([O:38][C:39]1[CH:40]=[CH:41][C:42]([C:45](=[O:50])/[CH:46]=[C:47](\[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])/[CH3:48])=[CH:43][CH:44]=1)([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acidHCID 183763601(4-Isopropoxyphenyl)-1,3-butanedione

Product 1

HCID 69837808(2S)-2-{[(Z)-3-(4-isopropoxyphenyl)-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 435 mg (0.91 mmol) of Intermediate 45 (as the TFA salt) and 200 mg (0.91 mmol) of Intermediate 29 to yield 125 mg of Example 27 as a beige glassy solid: TLC (DCM/MeOH (4:1): Rf=0.50; 1H NMR (DMSO-d6, 400 MHz) δ11.29 (d, 1H, J=8.8), 7.88 (m, 2H), 7.70 (d, 2H, 8.8), 7.48 (m, 3H), 7.09 (d, 2H, J=8.0), 6.85 (d, 2H, J=8.8), 6.78 (d, 2H, J=8.0), 5.46 (s, 1H), 4.62 (septuplet, 1H, J=6.4), 4.12 (t, 2H, J=6.4), 4.0 (m, 1H), 3.14 (m, 2H), 2.87 (t, 2H; J=6.4), 2.70 (dd, 1H, J=13.2, 9.6), 2.31 (s, 3H), 1.61 (s, 3H), 1.21 (d, 6H, J=6.4); low resolution MS (ES+)m/e 569 (MH+).

Sources & evidence

ORD record
ord-f8f7a76cdf68451fa57ce2d4bd8ebd37
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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