3-(4-benzyloxyphenyl)propanoic acid derivative
A technology of propionic acid and methoxy, applied in the direction of organic chemistry, etc., can solve the problems such as no disclosure of GPR40 receptor function regulation, no reported compounds, etc.
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Embodiment 1
[0772] 3-(4-{[2′-Methyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methoxy}phenyl)propanoic acid methyl ester
[0773]
[0774] Methyl 3-(4-hydroxyphenyl)propionate (1.43 g, 7.94 mmol), [2′-methyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl- A solution of 3-yl]methanol (2.37 g, 7.94 mmol) and tributylphosphine (2.97 ml, 11.9 mmol) in toluene (120 ml) was stirred under ice-cooling, and 1,1'-( azodicarbonyl) bipiperidine (3.00 g, 11.9 mmol). The mixture was warmed to room temperature and stirred for 24 hours. Hexane (60 mL) was added to the reaction mixture, and the precipitated insoluble matter was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified using silica gel column chromatography (hexane-20% ethyl acetate / hexane) to obtain the title compound (3.05 g, yield 83%) as a colorless oil.
[0775] 1 H NMR (CDCl 3 )δ: 1.58-1.75 (3H, m), 1.85-1.90 (2H, m), 1.97-2.08 (1H, m), 2.23 (3H, s), 2.60 (2H, t, J=7.8Hz), 2.89 (2H, t, J=...
Embodiment 2
[0777] 3-(4-{[2′-Methyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methoxy}phenyl)propanoic acid
[0778]
[0779]To 3-(4-{[2'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methoxy}phenyl)propionic acid methyl ester (0.599 g, 1.30 mmol) in methanol (6 mL) and tetrahydrofuran (6 mL) was added 2M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 24 hours. Water was added to the reaction mixture, and the mixture was neutralized with 10% aqueous citric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain colorless needle crystals of the title compound (0.436 g, yield 75%).
[0780] 1 H NMR (CDCl 3 )δ: 1.58-1.76 (3H, m), 1.85-1.90 (2H, m), 1.97-2.10 (1H, m), 2.23 (3H, s), 2.65 (2H, t, J=7.6Hz), 2.91 (2H, t, J=7.6Hz), 3.60-3.66(1H, m), 3.91-3.99(1H...
Embodiment 3
[0782] Methyl 3-{4-[(4′-hydroxy-2′-methylbiphenyl-3-yl)methoxy]phenyl}propanoate
[0783]
[0784] Methyl 3-(4-{[2'-methyl-4'-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methoxy}phenyl)propionate (3.78 g, 8.21 mmol) and p-toluenesulfonic acid monohydrate (0.156 g, 0.821 mmol) in methanol (60 mL) were stirred at room temperature for 2 hours. The reaction solvent was evaporated under reduced pressure, and the residue was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-60% ethyl acetate / hexane) to obtain the title compound (3.04 g, yield 98%) as a colorless viscous oil.
[0785] MS m / z 377 (MH + )
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