(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid → HCID 69838329, compound

HRID 2300641Notes

Reaction equation

HRID 2300641 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])[CH:32]=[CH:31][C:30]=1[C:36](=[O:40])[C:37]#[C:38][CH3:39]>>[F:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[C:36](=[O:40])/[CH:37]=[C:38](\[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])/[CH3:39]

Participants

3

Reactant 2

HCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acidHCID 18376325HCID 18376325, compound

Product 1

HCID 69838329HCID 69838329, compound

Procedure

The title compound was prepared (as described above for the preparation of Example 12) from 120 mg (0.33 mmol) of Intermediate 45 and 59 mg (0.33 mmol) of Intermediate 39 to yield 63 mg (35% yield) of Example 31: TLC (DCM/MeOH (4:1): Rf=0.72; 1H NMR (DMSO-d6, 400 MHz) δ11.37 (d, 1H, J=9.4), 7.87 (m, 2H), 7.72 (q, 1H, J=6.4), 7.43 (m, 3H), 7.14 (m, 4H), 6.79 (d, 2H, J=8.8), 5.25 (s, 1H), 4.13 (m, 3H), 3.18 (m, 1H), 2.85 (t, 2H, J=6.0), 2.77 (dd, 1H, J=14.0, 9.8), 2.29 (s, 3H), 1.62 (s, 3H) ; low resolution MS (ES−)m/e 545.1 (M-H).

Sources & evidence

ORD record
ord-227cd3f6cd164a77a7839e039cfe58b6
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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