A kind of (e)-tert-butyl-5-(2-nitrovinyl)-1h-imidazole-1-carboxylic acid tert-butyl ester and preparation method thereof
A technology of imidazole carboxaldehyde and di-tert-butyl ester, which is applied in the field of -tert-butyl-5--1H-imidazole-1-carboxylic acid tert-butyl ester compound and its preparation field, can solve the problem of low reaction yield, unsuitability for industrial production, Difficulty in purification and other problems, to achieve the effect of simple post-processing, convenient large-scale production and simple process
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Embodiment 1
[0030] A kind of synthetic method of (E)-tert-butyl-5-(2-nitrovinyl)-1H-imidazole-1-formic acid tert-butyl ester compound, specifically comprises the steps:
[0031] (1) 4-imidazole formaldehyde (10g) and triethylamine (2.89mL) were dissolved in 100mL of organic solvent tetrahydrofuran, then di-tert-butyl dicarbonate (28.9mL) was added, and the reaction was carried out at 30°C for 3h with stirring, and the reaction was completed After the organic solvent was removed by rotary evaporation, 50 mL of saturated sodium carbonate solution was added, and then extracted three times with 20 mL of dichloromethane, and the organic phases obtained from the three extractions were combined, dried with sodium sulfate, filtered, and concentrated to obtain a white solid;
[0032] The amount of 4-imidazole formaldehyde, triethylamine and di-tert-butyl dicarbonate used in the above-mentioned acylation reaction is calculated in molar ratio, that is, 4-imidazole formaldehyde: triethylamine: di-tert...
Embodiment 2
[0042] A kind of synthetic method of (E)-tert-butyl-5-(2-nitrovinyl)-1H-imidazole-1-formic acid tert-butyl ester compound, specifically comprises the steps:
[0043] (1) 4-imidazole formaldehyde (10g) and 4-dimethylaminopyridine (1.3g) were dissolved in 150mL organic solvent tetrahydrofuran, then di-tert-butyl dicarbonate (26.7mL) was added, and reacted at 30°C for 3h After the reaction was completed, the organic solvent was removed by rotary evaporation, and 50 mL of saturated sodium carbonate solution was added, then extracted three times with 20 mL of dichloromethane, and the organic phases obtained from the combined three extractions were dried with sodium sulfate, filtered, and concentrated to obtain 18.5 g of a white solid;
[0044] The amount of 4-imidazole formaldehyde, 4-dimethylaminopyridine and di-tert-butyl dicarbonate used in the above condensation reaction is calculated in molar ratio, that is, 4-imidazole formaldehyde: 4-dimethylaminopyridine: di-tert-butyl dicar...
Embodiment 3
[0050] The (E)-tert-butyl-5-(2-nitrovinyl)-1H-imidazole-1-carboxylic acid tert-butyl ester compound obtained in Example 1 was used to prepare tert-butyl-5-(2-aminoethyl Base)-1H-imidazole-1-carboxylic acid tert-butyl ester, its synthetic method is as follows:
[0051] (E)-tert-butyl-5-(2-nitrovinyl)-1H-imidazole-1-carboxylic acid tert-butyl ester (20g) and reducing agent lithium aluminum hydride (0.95g) in 40mL tetrahydrofuran, at room temperature After reacting for 6 hours, the resulting reaction solution was quenched with water at 0°C, and extracted three times with dichloromethane (20 mL) after the solvent was removed by spin. The extract was concentrated to obtain 16.9 g of white solid.
[0052] The white solid of above-mentioned gained detects through NMR instrument, and its 1 The result of H-NMR is as follows:
[0053] 1H-NMR (DMSO-D 6 ,25℃):1.63(s,9H),2.74(m,2H),3.03(m,2H),7.33(s,1H),7.88(s,1H);
[0054] From the above test results, it can be concluded that the whit...
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