A hydrogen bond organic catalyst derived from pyroglutamic acid and its preparation method and application
An organic catalyst, pyroglutamic acid technology, applied in organic chemistry methods, organic compound/hydride/coordination complex catalysts, organic chemistry and other directions, to achieve the effect of simple synthesis process, easy preparation and novel structure
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Embodiment 1
[0033]
[0034]L-pyroglutamic acid (0.65g, 5.0mmol) and p-toluenesulfonamide (1.03g, 6.0mmol) were dissolved in 10mL of dichloromethane, and 4-dimethylaminopyridine (DMAP, 0.18 g, 1.5 mmol) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.08 g, 6.0 mmol). After stirring at room temperature for 72 hours, 100 mL of ethyl acetate and 15 mL of 1M hydrochloric acid were added to the reaction mixture. The organic phase was washed with half-saturated brine (3×30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was separated by silica gel column chromatography with gradient elution of methanol-dichloromethane (1:99-5:95) to obtain 0.46 g of white solid with a yield of 33%. The melting point is 84-85°C. [α] D 20 =-41.4(c=0.5in MeOH); IR(KBr)ν3430,2921,1633,1263,1010,896,843,812cm -1 ; 1 H NMR (400MHz, DMSO-d 6 )δ12.32(br s,1H),7.82(d,J=8.4Hz,2H),7.77(s,1H),7.44(d,J=8.4Hz,2H),4.04(dd,J=9.0, 4.2Hz,1H),2....
Embodiment 2
[0036]
[0037] L-pyroglutamic acid (0.65g, 5.00mmol) and p-methoxybenzenesulfonamide (1.12g, 6.0mmol) were dissolved in 10mL of dichloromethane, and 4-dimethylaminopyridine (DMAP, 0.18 g, 1.5 mmol) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI, 1.08 g, 6.0 mmol). After stirring at room temperature for 72 hours, 100 mL of ethyl acetate and 15 mL of 1M hydrochloric acid were added to the reaction mixture. The organic phase was washed with half-saturated brine (3×30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was separated by silica gel column chromatography with gradient elution of methanol-dichloromethane (1:99-5:95) to obtain 0.59 g of white solid with a yield of 40%. The melting point is 113-115°C. [α] D 20 =-43.1 (c=0.5inMeOH); IR(KBr)ν3417,1656,1499,1262,1148,836cm -1 ; 1 H NMR (400MHz, DMSO-d 6 )δ7.87(dd, J=6.8,2.0Hz,2H),7.76(s,1H),7.14(dd,J=6.8,2.0Hz,2H),4.03(dd,J=8.8,4.0Hz,1H ),3....
Embodiment 3
[0039]
[0040] L-pyroglutamic acid (0.65g, 5.0mmol) and p-nitrobenzenesulfonamide (1.21g, 6.0mmol) were dissolved in 10mL of dichloromethane, and 4-dimethylaminopyridine (DMAP, 0.18 g, 1.5 mmol) and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.08 g, 6.0 mmol). After stirring at room temperature for 72 hours, 100 mL of ethyl acetate and 15 mL of 1M hydrochloric acid were added to the reaction mixture. The organic phase was washed with half-saturated brine (3×30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was separated by silica gel column chromatography with gradient elution of methanol-dichloromethane (1:99-5:95) to obtain 0.64 g of white solid with a yield of 41%. Melting point 108-109°C. [α] D 20 =-25.6 (c=0.5inMeOH); IR(KBr)ν3392,2867,1681,1352,1260,1140,847,738cm -1 ; 1 H NMR (400MHz, DMSO-d 6 )δ12.74(br s,1H),8.45(d,J=8.8Hz,2H),8.19(d,J=8.8Hz,2H),7.77(s,1H),4.07(dd,J=9.2, 4.4Hz, 1H)...
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