4-Nitrophenyl chloroformate → HCID 21969273, compound

Participants

Reaction Steps

p-Nitrophenyl chloroformate (252 mg, 1.25 mmol) in anhydrous methylene chloride was added to a stirred solution of 3'-O-(t-butyldimethylsilyl)thymidine (356 mg, 10 mmol, Wang et al. Nucleosides Nucleotides 1998, 17, 1033-1051) in anhydrous methylene chloride (4 mL) and pyridine (0.5 mL). The resulting solution was stirred at room temperature overnight, then cooled with ice, quenched with water (2 mL), stirred at 0° C. for 30 min, diluted with methylene chloride, washed with dilute acetic acid, water, then 5% sodium bicarbonate, dried over sodium sulfate, and concentrated to dryness. Chromatography on silica with ethyl acetate-hexanes (1:1 to 3:2) gave 505 mg of the titled compound as a colorless foam.

Provenance & Evidence