Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-phenylcarbamoyl-uridine

Participants

Reaction Steps

The THF solution (1 ml) containing 2,2′-isopropylidenebis[(4S)-4-tert-butyl-2-oxazoline] (0.03 mmol, 8.9 mg) and Cu(OTf)2 (II) (0.03 mmol, 11.1 mg) was stirred for 2 hours at room temperature. After the reaction mixture was cooled to 0° C., the THF solution (1 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.3 mmol, 164 mg) and the THF solution of phenyl isocyanate (0.3 mmol, 35.7 mg) were added thereto. After the mixture was continuously stirred at 0° C. overnight, the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-2′-O-phenylcarbamoyl-uridine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-3′-O-phenylcarbamoyl-uridine were produced at the ratio of 72:28, and the transformation ratio of the reaction was 95%.

Provenance & Evidence