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

HRID 2300631Notes

Reaction equation

HRID 2300631 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].[F:28][C:29]1[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=1[C:37](=[O:41])[C:38]#[C:39][CH3:40]>>[CH3:40]/[C:39](/[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:38]/[C:37](=[O:41])[C:30]1[CH:31]=[C:32]([F:36])[C:33]([F:35])=[CH:34][C:29]=1[F:28]

Participants

3

Reactant 2

HCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acidHCID 183763671-(2,4,5-Trifluorophenyl)-2-butyn-1-one

Product 1

HCID 9894127(2S)-2-{[(Z)-1-methyl-3-oxo-3-(2,4,5-trifluorophenyl)-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 12) from 677 mg (1.85 mmol) of Intermediate 45 and 366 mg (1.85 mmol) of Intermediate 38 to yield 482 mg (46% yield) of Example 16. TLC (DCM/MeOH (4:1): Rf=0.55; 1H NMR (DMSO-d6, 300 MHz) δ11.39 (d, 1H, J=8.9), 7.86 (m, 2H), 7.69-7.59 (m, 1H), 7.54-7.40 (m, 4H), 7.10 (d, 2H, J=8.5), 6.79 (d, 2H, J=8.5), 5.3 (s, 1H), 4.12 (t, 2H, J=6.5), 4.1 (m, 1H), 3.16 (m, 1H), 2.86 (t, 2H, J=6.5), 2.76 (dd, 1H, J=13.7, 8.9), 2.3 (s, 3H), 1.64 (s, 3H): low resolution MS (ES+)m/e 565.1 (MH+).

Sources & evidence

ORD record
ord-8befbde03d734d0ba6adf1a310816586
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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