Method for purifying trityl group-containing monodispersed polyethylene glycol
A technology of trityl and polyethylene glycol, used in ether separation/purification, organic chemistry, ether preparation, etc., can solve the problems of difficult removal, difficult manufacturing, and unsuitable for amplification, and achieves good repeatability.
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Embodiment 1
[0129] The synthesis of embodiment 1 compound 2
[0130]
[0131] Tetraethylene glycol 1 (2,000 mL, 11.5 mol) was put into a four-neck flask, and azeotropic dehydration was performed twice using toluene (500 mL×2 times). The inside of the eggplant-shaped flask was purged with nitrogen, pyridine (180 mL, 2.2 mol) and trityl chloride (TrtCl, 400 g, 1.4 mol) were added, and the mixture was stirred at room temperature for 3 hours. After 3 hours, disappearance of TrtCl was confirmed by using thin layer chromatography (TLC, hexane:ethyl acetate=1:1 (volume ratio)), and 2,000 mL of ion-exchanged water was added. After adding toluene (1,000 mL) to the resulting mixture, the layers were separated, and the organic layer was washed once with a mixed solution of 1,000 mL of ion-exchanged water / saturated brine (ion-exchanged water:saturated brine=4:1 (volume ratio)), Wash once with 500 mL of 1M aqueous hydrochloric acid solution, and wash four times with 500 mL of saturated saline. So...
Embodiment 2
[0149] The synthesis of embodiment 2 compound 4
[0150]
[0151] The reaction product containing the above compound 2 (compound 2: 628 g, less than 0.14 mol) and 2,000 mL of tetrahydrofuran (THF) were placed in an eggplant-shaped flask, and the whole was cooled to 0°C. Aqueous sodium hydroxide solution (200 g, 5.0 mol / 600 mL) was added, followed by stirring at 0° C. for 20 minutes. To the reaction mixture was added dropwise a toluenesulfonyl chloride (TsCl) / THF solution (300 g, 1.6 mol / 600 mL) during 30 minutes, and the mixture was stirred at 0° C. for 4 hours. After 4 hours, disappearance of Compound 2 was confirmed by using TLC (hexane:ethyl acetate=1:1 (volume ratio)), and then, the mixture was stirred at room temperature for 15 hours to disappear unreacted TsCl. After 15 hours, the disappearance of TsCl was confirmed by TLC, and 300 mL of ion-exchanged water and 500 mL of diethyl ether were added. The mixed solution was washed once with 500 mL of saturated aqueous so...
Embodiment 3
[0153] Synthesis of monodisperse PEG (compound 5) comprising a terminal trityl group with a chain length of 8 in embodiment 3
[0154]
[0155] Sodium hydride (81 g) was charged into a two-necked eggplant-shaped flask, and the inside was replaced with nitrogen. Washed twice with anhydrous hexane (500 mL x 2 times), added 1,800 mL of THF, and cooled the whole to 0°C. Tetraethylene glycol 1 (2,000 mL, 11.5 mol) azeotropically dehydrated three times with 500 mL of toluene was placed in a dropping funnel and added thereto dropwise during 30 minutes. After the dropwise addition was completed, the reaction product containing Compound 4 obtained in Example 2 (Compound 4: 813 g, less than 1.4 mol) obtained in Example 2 that had been azeotropically dehydrated three times with 500 mL of toluene was mixed with 1,000 mL of THF, and the resultant was placed in the same in a dropping funnel and added dropwise over a 15 minute period. After the dropwise addition was complete, the reacti...
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