Preparation method of biapenem
A biapenem and organic solvent technology, applied in the field of preparation of biapenem, can solve the problems of complex equipment, water removal, low drying rate, etc., to improve the crystallization yield and purity, reduce the amount of water, improve the The effect of production efficiency
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Embodiment 1
[0049] 6-[(4R, 5S, 6S)-2-(4-nitrobenzyloxycarbonyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-nitrogen Heterobicyclo[3,2,0]hept-2-en-3-yl]thio-6,7-dihydro-5H-pyrazolo[1,2-α][1,2,4]tri Azol-4-ium chloride (I, R=O 2 NPhCH 2 ) 300g (0.58mol), was added into 1.5L of water and 1.0L of tetrahydrofuran, stirred and dissolved, and 70g of palladium carbon (10%) was added, and the hydrogenation pressure was controlled at 4-5Kg / m 2 , react at 10-20°C for 2.5 hours; filter off palladium-carbon immediately after the reaction, adjust the pH to 3.0-6.0 with 4-dimethylaminopyridine, separate the liquids, add 4.0L of acetone to the water phase, and stir at 10-20°C for 3.0 hours. Crystals were precipitated, filtered, the solid was washed with 300 ml of acetone, and dried under reduced pressure to obtain 180 g of biapenem (yield: 90%).
Embodiment 2
[0051] 6-[(4R, 5S, 6S)-2-(4-nitrobenzyloxycarbonyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-nitrogen Heterobicyclo[3,2,0]hept-2-en-3-yl]thio-6,7-dihydro-5H-pyrazolo[1,2-α][1,2,4]tri Azol-4-ium chloride (I, R=O 2 NPhCH 2 ) 600g (1.16mol), was added into 3.0L of water and 2.0L of tetrahydrofuran, stirred and dissolved, and 120g of palladium hydroxide (10%) was added, and the hydrogenation pressure was controlled at 10-15Kg / m 2 , react at 10-15°C for 1.0 hour; after the reaction, use N-methylmorpholine to adjust the pH to 3.0-6.0, filter off the palladium hydroxide, separate the liquids, add 8.0L ethanol to the water phase, stir at 0-5°C for 0.5 hours, Crystals were precipitated, filtered, the solid was washed with 600 ml of ethanol, and dried under reduced pressure to obtain 364 g of biapenem (yield: 91.0%).
Embodiment 3
[0053] 6-[(4R, 5S, 6S)-2-(4-nitrobenzyloxycarbonyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-nitrogen Heterobicyclo[3,2,0]hept-2-en-3-yl]thio-6,7-dihydro-5H-pyrazolo[1,2-α][1,2,4]tri Azol-4-ium chloride (I, R=O 2 NPhCH 2 ) 600g (1.16mol), add to water 3.0L and tetrahydrofuran 2.0L, stir to dissolve, add platinum carbon (5%) 200g, control hydrogenation pressure 20Kg / m 2 , react at 25-30°C for 0.5 hours; filter the platinum carbon within 10 minutes after the end of the reaction, adjust the pH to 4.0-6.0 with N-methylpiperidine, separate the liquid, add 8.0L ethanol to the water phase, stir at 5-10°C for 2.0 After hours, crystals were precipitated, filtered, the solid was washed with 600 ml of ethanol, and dried under reduced pressure to obtain 360 g of biapenem (yield: 90%).
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