A kind of preparation method of avibactam intermediate
A technology for an intermediate and a synthesis method, which is applied in the field of preparation of avibactam intermediates, can solve the problems of difficult reaction control, low yield and the like, and achieves the effects of mild reaction conditions, easy purification and high yield
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Embodiment 1
[0045]9.97g (40mmol) of compound I, 50ml of acetonitrile, and 5.687g (44mmol) of diisopropylethylamine were put into the reaction flask, the temperature was lowered to below 0°C, and 9.307g (42mmol) of p-nitrobenzenesulfonyl chloride was added until the reaction was complete ( Monitored by TLC (dichloromethane:methanol=10:1). Add 8.43 g (52 mmol) of carbonyldiimidazole and raise the temperature to 45° C. to react until the reaction is complete (monitored by TLC (dichloromethane:methanol=10:1)). Add 5.85 g (80 mmol) of diethylamine, and react at a temperature of 45° C. until the reaction is complete (monitored by TLC (dichloromethane:methanol=10:1)). Cool down to room temperature, add dichloromethane and water, separate phases, decompress the organic phase to dryness, add 5ml of ethyl acetate, heat up to dissolve, add 20ml of n-hexane to precipitate, filter at 0°C, and dry at 45°C to obtain the compound IV 9.2g, yield 88.4%, content>98%. The NMR data are: 1 H NMR (400MHz, DM...
Embodiment 2
[0047] Put 9.97g (40mmol) of compound I, 50ml dichloromethane, and 5.687g (44mmol) of diisopropylethylamine into the reaction flask, cool down to below 0°C, add 9.307g (42mmol) of p-nitrobenzenesulfonyl chloride, until the reaction completely. Add 8.43 g (52 mmol) of carbonyldiimidazole and raise the temperature to 45°C for reaction until the reaction is complete. Add 5.85 g (80 mmol) of diethylamine, and control the temperature at 45°C to react until the reaction is complete. Cool down to room temperature, add water, separate phases, depressurize the organic phase to dryness, add 5ml of ethyl acetate, heat up to dissolve, add 20ml of n-hexane to precipitate, suction filter at 0°C, and dry at 45°C to obtain 9.7g of compound IV. Yield 93.2%, content > 98.5%
Embodiment 3
[0049] Put 9.97g (40mmol) of compound I, 50ml acetonitrile, and 5.687g (44mmol) of diisopropylethylamine into the reaction flask, cool down to below 0°C, and add 9.307g (42mmol) of p-nitrobenzenesulfonyl chloride until the reaction is complete. Add 8.43 g (52 mmol) of carbonyldiimidazole and raise the temperature to 45°C for reaction until the reaction is complete. An aqueous solution (80 mmol) of 8.0 g of potassium bicarbonate was added, and the temperature was controlled at 45° C. to react until the reaction was complete. Cool down to room temperature, add dichloromethane and water, separate phases, decompress the organic phase to dryness, add 5ml of ethyl acetate, heat up to dissolve, add 20ml of n-hexane to precipitate, filter at 0°C, and dry at 45°C to obtain the compound IV 9.0g, yield 86.4%, content>98.5%
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