Dual-protection ertapenem crystal and preparation method thereof
A technology for ertapenem and ertapenem side chains, applied in the field of a double-protected ertapenem crystal and a preparation method thereof, can solve the unreported amorphous stability data of double-protected ertapenem , Unable to obtain stable double-protected ertapenem, unreported double-protected ertapenem purification method, etc., to achieve the effect of easy to achieve large-scale, cheap raw materials, and practical promotion value
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Embodiment 1
[0054]Under the protection of argon, dissolve 25.0g (42.0mmol) of carbapenem core MAP and 19.0g (42.6mmol) of ertapenem side chain in 200ml DMF, then cool down to 0-5°C; DMF (35ml) solution of 13.4g (133mmol) of isopropylamine. After the reaction is completed, the reaction solution is poured into a solution of potassium dihydrogenphosphate buffer solution (pH=4.0, 1500ml) and ethyl acetate precooled to 10°C. In the mixed solvent formed by 500ml, extract and separate layers, then add 200ml of the above buffer solution to the organic layer to wash; Add 180ml of n-hexane dropwise, filter after dropping, wash the filter cake with 60ml of a mixed solvent (volume ratio 1:1) of ethyl acetate and n-hexane with a volume ratio of 1:1, and finally dry it under vacuum at 20°C to obtain a white solid 30.7 g of double-protected ertapenem, the molar yield based on side chains was 92%, and the HPLC purity was 98.5%.
Embodiment 2
[0056] Under the protection of argon, dissolve 25.0g (42.0mmol) of carbapenem core MAP and 18.9g (42.4mmol) of ertapenem side chain in 200ml DMF, then cool down to 0-5°C; DMF (35ml) solution of 8.5g (84mmol) of isopropylamine. After the reaction is completed, the reaction solution is poured into a solution of dipotassium hydrogen phosphate buffer solution (pH=6.0, 1000ml) and methyl formate, which is pre-cooled to 15°C. In the mixed solvent formed by 1000ml, extract and separate layers, and then add 200ml of the above buffer solution to the organic layer to wash; Add 180ml of n-pentane dropwise, filter after dropping, wash the filter cake with a mixed solvent (1:1 by volume) of methyl formate and n-pentane with a volume ratio of 1:1 with 60ml, and finally dry it in vacuum at 25°C to obtain White solid double-protected ertapenem 30.0g, the molar yield based on the side chain is 90%, and the HPLC purity is 98.0%.
Embodiment 3
[0058] Under the protection of argon, dissolve 25.0g (42.0mmol) of carbapenem core MAP and 19.1g (42.9mmol) of ertapenem side chain in 200ml DMF, then cool down to 0-5°C; 12.7g (126mmol) of isopropylamine in DMF (35ml) solution. After the reaction is completed, the reaction solution is poured into a solution of sodium dihydrogen phosphate buffer (pH = 4.5, 1000ml) and ethyl formate In the mixed solvent formed by 2000ml, extract and separate layers, then add 200ml of the above buffer solution to the organic layer to wash; the organic layer is dried with anhydrous sodium sulfate, filtered, stirred and crystallized at 20-25°C for 6h, and then heated at 20-25°C Add 180ml of n-heptane dropwise, filter after dropping, wash the filter cake with a mixed solvent (1:1 by volume ratio) of ethyl formate and n-heptane with a volume ratio of 1:1 with 60ml, and finally dry it under vacuum at 30°C to obtain 29.5 g of white solid double-protected ertapenem, the molar yield based on side chains...
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