Method for preparing capecitabine intermediate 2', 3'-di-O-acetyl-5'-deoxy-5-fluorocytidine by enzymatic composite chemical method
A capecitabine and chemical method technology, applied in the field of medicinal chemistry, can solve the problems of complicated and complicated preparation method of -deoxy-5-fluorocytidine, unsuitable for production conditions, unsuitable for environmental protection requirements, etc. The effect of high purity, easy control and few by-products
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Embodiment 1
[0020] Add 5mM 5 ’ -Deoxyribose-1-phosphate was reacted with 5mM 5-fluorocytosine, 25 units / mL pyrimidine nucleoside phosphorylase, 5mM CaCl2, at 28°C for 12 hours. After the end of the reaction, a white precipitate was visible at the bottom of the reactor. The white precipitate was filtered off, and the filtrate was concentrated to dryness at 55°C under reduced pressure. The obtained residue was dissolved in 5ml of methanol, dried by adding 2g of anhydrous sodium sulfate, filtered, and 5ml of isopropyl ether was added dropwise to the filtrate while stirring, and filtered after 2h. The solid was mixed with 40 ℃ vacuum drying for 4 hours, that is, 4.8mM of 5 ’ - Deoxy-5-fluoro-cytidine (yield 96%, HPLC 99.4%). mp192-193°C (literature: 192-194°C). HNMR(DMSO-d6)δ: 1.276 (d, 3H, H-11), 3.644 (m, 1H, H-3), 3.809 (m, 1H, H-4), 3.992 (m, 1H, H-2 ), 4.980 (d, 1H, H-10), 5.277 (d, 1H, H-9), 5.677 (s, 1H, H-1) 7.559 (s, J=7.0Hz, 1H, H-8), 7.753 (m, 2H, H-12).
[0021]
Embodiment 2
[0023] Add 5mM 5 ’ -Deoxyribose-1-phosphate was reacted with 5mM 5-fluorocytosine, 25 units / mL pyrimidine nucleoside phosphorylase, 5mM CaCl2, at 28°C for 12 hours. After the end of the reaction, a white precipitate was visible at the bottom of the reactor. The white precipitate was filtered off, and the filtrate was concentrated to dryness at 55°C under reduced pressure. The obtained residue was dissolved in 5ml of methanol, dried by adding 2g of anhydrous sodium sulfate, filtered, and 5ml of isopropyl ether was added dropwise to the filtrate while stirring, and filtered after 2h. The solid was mixed with 40 ℃ vacuum drying for 4 hours, that is, 4.6mM of 5 ’ -Deoxy-5-fluoro-cytidine (yield 92%, HPLC 99.2%).
Embodiment 3
[0025] Add 5mM 5 ’ -Deoxyribose-1-phosphate was reacted with 5mM 5-fluorocytosine, 25 units / mL pyrimidine nucleoside phosphorylase, 5mM CaCl2, at 28°C for 12 hours. After the end of the reaction, a white precipitate was visible at the bottom of the reactor. The white precipitate was filtered off, and the filtrate was concentrated to dryness at 55°C under reduced pressure. The obtained residue was dissolved in 5ml of methanol, dried by adding 2g of anhydrous sodium sulfate, filtered, and 5ml of isopropyl ether was added dropwise to the filtrate while stirring, and filtered after 2h. The solid was mixed with 40 ℃ vacuum drying for 4 hours, that is, 4.7mM of 5 ’ -Deoxy-5-fluoro-cytidine (yield 94%, HPLC 99.5%).
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