5'-O-(4,4'-Dimethoxytrityl)-2'-O-[2-(N-methylcarbamoyl)ethyl]uridine → HCID 178485725, compound

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Reaction Steps

The compound (490 mg, 0.77 mmol) prepared in Example 8 was dissolved in dried acetonitrile (2 mL), and 2-cyanoethoxy N,N,N′,N′-tetraisopropylphosphorodiamidite (358 mg, 1.19 mmol) dissolved in dried acetonitrile (2 mL) was added thereto. To the mixture was further added diisopropylammonium 1H-tetrazolide (101 mg, 0.59 mmol), followed by stirring at room temperature for 8 hours. The reaction was terminated by adding water thereto, and dilution with ethyl acetate was carried out. The organic layer was washed with saturated brine three times and a saturated sodium hydrogen carbonate aqueous solution three times. The organic layer was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography eluting with chloroform:methanol (99:1, v/v) containing 0.5% triethylamine to give the title compound (384 mg, 66%).

Provenance & Evidence