Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N4-[bis(4-methoxy-phenyl)phenylmethyl]-3'-O-phenylcarbamoylcytidine

Participants

Reaction Steps

The dioxane solution (4 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.02 mmol, 6.2 mg) and Cu(OTf)2 (II) (0.02 mmol, 7.4 mg) was stirred for 1.25 hours at room temperature. The dioxane solution (1 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N4-[bis(4-methoxy-phenyl)phenylmethyl]cytidine (0.2 mmol, 169.6 mg) and the dioxane solution (1 ml) of phenyl isocyanate (0.2 mmol, 23.8 mg) were added thereto. After the mixture was continuously stirred for 4 hours at room temperature, the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N4-[bis(4-methoxy-phenyl)phenylmethyl]-2′-O-phenylcarbamoylcytidine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N4-[bis(4-methoxy-phenyl)phenylmethyl]-3′-O-phenylcarbamoylcytidine were produced at the ratio of 85:15, and the transformation ratio of the reaction was 93%.

Provenance & Evidence