Method for purifying protected 2'-deoxycytidines
A technology of deoxycytidines and deoxycytidines, which is applied in the field of crystallization of protected 2'-deoxycytidines and the formation of complexes with water, and can solve problems such as unknown crystallization
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reference example 1
[0089] N 4 -Production of benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine
[0090] 119.0g of N 4 -Benzoyl-2'-deoxycytidine was dissolved in 1.5 L of pyridine. After adding 113.5 g of 4,4'-dimethoxytrityl chloride over 2 hours at room temperature, the mixture was stirred at room temperature for 4 hours. After adding 33.8 g of sodium bicarbonate, the mixture was stirred for another 2 hours, and then the reaction solution was concentrated. 1.2 L of ethyl acetate and 300 mL of water were added to the residue, followed by stirring. A small amount of saturated brine was added for liquid separation, and the organic layer was washed with water again, and dried over anhydrous magnesium sulfate. After filtering and distilling off the solvent, it was purified by silica gel column chromatography using ethyl acetate solvent. While vigorously stirring, the fraction containing the target product was dropped into 2.0 L of diisopropyl ether, followed by stirring at room temperature f...
Embodiment 1
[0092] N 4 Synthesis of crystals of -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine complexed with water
[0093] The N synthesized in the reference example 1 4 -The free form of benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine (2.0g), dissolved in 1,2-dichloroethane ( 5 mmL), water (0.1 g) was added, and crystallization was carried out at -24°C for 1 day. After the obtained crystals were collected by filtration, they were dried under reduced pressure at 50°C to obtain N 4 Crystals of -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine complexed with water (0.8 g). By Karl Fischer analysis, the moisture value was 2.7%. In addition, the crystals have clear crystallinity peaks in XRD measurement, especially rapid absorption at 5.6°, 7° and 10.3°. In addition, as measured by DSC, there was an endothermic peak accompanying crystal melting at 109°C.
[0094] The N contained in this complex 4 -Benzoyl-2'-deoxycytidine, N 4 -Benzoyl-3'-O-(4,4'-dimethoxytrityl)-2'-...
Embodiment 2
[0096] N 4 Synthesis of crystals of -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine complexed with water
[0097] The N synthesized in the reference example 1 4 The free form (2.0 g) of -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine was dissolved in butyl acetate (5 mmL), and the alkane (0.5ml), add water (0.1g) and the N obtained in Example 14 Crystallization of -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine complexed with water (10 mg), crystallized under ice-cooling day. After the obtained crystals were collected by filtration, they were dried under reduced pressure at 50°C to obtain N 4 Crystals of -benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine complexed with water (1.3 g). Moisture value by Karl Fischer analysis was 2.2%. In addition, the crystals have clear crystallinity peaks in XRD measurement, especially rapid absorption at 5.6°, 7°, and 10.3°. In addition, as measured by DSC, there was an endothermic peak accompanying crystal melting ...
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