1-(4-Methoxyphenyl)butane-1,3-dione → HCID 69835561, compound

HRID 2300646Notes

Reaction equation

HRID 2300646 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].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:41])[CH2:37][C:38](=O)[CH3:39])=[CH:32][CH:31]=1>>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:41])/[CH:37]=[C:38](\[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])/[CH3:39])=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 776401-(4-Methoxyphenyl)butane-1,3-dioneHCID 18343040(2S)-2-amino-3-{4-[2-(5-methyl-2-phenyl-1,3oxazol-4-yl)ethoxy]phenyl}propanoic acid

Product 1

HCID 69835561HCID 69835561, compound

Procedure

The title compound was prepared (as described above for the preparation of Example 2) from 100 mg (0.27 mmol) of Intermediate 45 and 52 mg (0.27 mmol) of Intermediate 22 to yield 126 mg of Example 41. TLC (EtOAc/MeOH (7:3): Rf=0.44: 1H NMR (DMSO-d6, 400 MHz) δ11.30 (d, 1H, J=7.00), 7.87 (m. 2H), 7.73 (d, 2H, J=8.72), 7.45 (m, 3H), 7.10 (d, 2H, J=8.37), 6.88 (d, 2H, J=8.89), 6.77 (d, 2H, J=8.37), 5.74 (s, 1H), 4.11 (m, 2H), 4.01(m, br, 1H), 3.13 (m, 1H), 2.86 (m, 2H), 2.72 (m, 1H), 2.31 (s, 3H), 1.65 (s, 3H); low resolution MS (ES−) m/e 539 (M-H); RP-HPLC (Vydac C-18, 25 cm×4.6 mm; 10-50% CH3CN in H2O) with 0.1% HCO2H buffer: 30 minutes

Sources & evidence

ORD record
ord-251899f57c7340609058df5d7e204368
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

Loading…