Anti-enterovirus 71 (EV71) valerolactam compounds, preparation method and uses thereof
A valerolactam, EV71 technology, applied in antiviral agents, resistance to vector-borne diseases, organic chemistry, etc., can solve the problem that virus transcription and replication cannot continue normally.
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Embodiment 1
[0112] Example 1 Preparation of N-Boc-L-(+)-dimethyl glutamate (1-2)
[0113]
[0114] At 0°C, slowly add acetyl chloride (5 mL) dropwise into methanol (100 mL), stir for 5 minutes, then add glutamic acid (10 g, 67.9 mmol), continue stirring and heat to reflux, and keep the reflux temperature for 2 hours . The reaction was stopped, the solvent was removed under reduced pressure, and recrystallized from ether. The obtained oil was dissolved in THF (150mL), TEA (28.5mL, 203.7mmol) was added dropwise at 0°C, kept stirring at 0°C for 5 minutes, and dicarbonate dicarbonate dissolved in THF (30mL) was added dropwise. Tert-butyl ester (17.8 g, 81.5 mmol), stirred to room temperature for 2.5 hours. After the reaction, the solvent was distilled off under reduced pressure, water (200 mL) was added to the residue, extracted from the aqueous phase with DCM (2×200 mL), the combined organic phases were dried over anhydrous sodium sulfate, and then concentrated to obtain the crude produ...
Embodiment 2
[0115] Example 2 Preparation of 2-tert-butoxycarbonylamino-4-cyanomethyl-glutaric acid dimethyl ester (1-3)
[0116]
[0117] At -78°C, lithium bis(trimethylsilyl)amide (78.5mL 1.0M solution in THF, 78.5mmol) was slowly added dropwise to N-Boc-L-(+)-dimethylglutamate ester (1-2) (10 g, 36.4 mmol) in anhydrous THF (200 mL), and the resulting solution was stirred at this temperature for 30 minutes. Then, keeping the temperature constant, bromoacetonitrile (3.4 mL) was slowly added dropwise, and the reaction mixture was stirred at -78° C. for 2 hours. After the reaction was complete, saturated ammonium chloride aqueous solution (50 mL) was added to quench the reaction, and stirred to room temperature. First remove the solvent under reduced pressure, then add water (200mL), extract the aqueous phase with DCM (2×200mL), and dry the combined organic phase with anhydrous sodium sulfate, then concentrate, and the obtained crude product is passed through a flash chromatography colu...
Embodiment 3
[0118] Example 3 Preparation of 2-tert-butoxycarbonylamino-3-(2-carbonyl-3-pyrrolidine)-propionic acid methyl ester (1-4)
[0119]
[0120] To a solution of dimethyl 2-tert-butoxycarbonylamino-4-cyanomethyl-glutarate (1-4) (5 g, 15.9 mmol) in methanol (80 mL) was added cobalt chloride hydrate (2 g, 7.9 mmol ), and then added sodium borohydride (6 g, 59.5 mmol) in portions to the obtained pink mixture at 0° C., and stirred at room temperature for 18 hours. The reaction was quenched by adding saturated aqueous ammonium chloride (30 mL), and stirred for 10 minutes. The solid impurities were removed by suction filtration, and the solvent was evaporated under reduced pressure. Water (100 mL) was added and extracted from the aqueous phase with DCM (3 x 100 mL), the combined organic phases were dried over anhydrous sodium sulfate and then concentrated to give the crude product which was purified by flash chromatography (EA) to give 2-tert Butoxycarbonylamino-3-(2-carbonyl-3-pyrr...
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