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

HRID 2300637Notes

Reaction equation

HRID 2300637 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].[N+:28]([C:31]1[CH:32]=[C:33]([C:37](=[O:41])[C:38]#[C:39][CH3:40])[CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]>>[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]([C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([N+:28]([O-:30])=[O:29])[CH:32]=1)=[O:41]

Participants

3

Reactant 2

HCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acidHCID 183763081-(3-Nitrophenyl)-2-butyn-1-one

Product 1

HCID 69837904(2S)-2-{[(Z)-1-methyl-3-(3-nitrophenyl)-3-oxo-1-propenyl]amino}-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Procedure

The title compound was prepared (as described above for the preparation of Example 12) from 120 mg (0.25 mmol) of Intermediate 45 and 48 mg (0.25 mmol) of Intermediate 42 to yield 67 mg of Example 25: TLC (DCM/MeOH (4:1): Rf=0.52; 1H NMR (DMSO-d6, 400 MHz) δ11.52 (d, 1H, J=9.1), 8.52 (s, 1H), 8.24 (d, 1H, J=8.2), 8.21 (d, 2H, J=7.7), 7.87 (d, 2H, J=7.7), 7.66 (t, 1H, J=7.9), 7.45 (m, 3H), 7.10 (d, 2H, J=8.2), 6.79 (d, 2H, J=8.3), 5.74 (s, 1H), 4.13 (t, 2H, J=6.6), 4.07 (br s, 1H), 3.15 (m, 1H), 2.87 (t, 2H, J=6.4), 2.75 (m, 1H), 2.31 (s, 3H), 1.68 (s, 3H).; low resolution MS (ES+)m/e 556.3 (MH+).

Sources & evidence

ORD record
ord-66111bdcaf80448db17407862c46049c
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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