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

HRID 889767Notes

Reaction equation

HRID 889767 reaction equation
C([C@H]1COC(C2C=CC=C(C3OC[C@H](C(C)C)N=3)N=2)=N1)(C)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[CH:46]=[CH:45][C:43](=[O:44])[NH:42][C:40]3=[O:41])[C@H:36]([OH:47])[C@@H:35]2[OH:48])=[CH:27][CH:26]=1.[C:63]1([N:69]=[C:70]=[O:71])[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)OC[C@H]2O[C@@H](N3C=CC(=O)NC3=O)[C@H](OC(=O)NC3C=CC=CC=3)[C@@H]2O)=CC=1>[Cu](Cl)Cl.C1COCC1>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]([C:55]2[CH:56]=[CH:57][C:58]([O:61][CH3:62])=[CH:59][CH:60]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[CH:46]=[CH:45][C:43](=[O:44])[NH:42][C:40]3=[O:41])[C@H:36]([OH:47])[C@@H:35]2[O:48][C:70](=[O:71])[NH:69][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 7672Phenyl isocyanateHCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridineHCID 117633095'-O-(Bis(4-methoxyphenyl)phenylmethyl)uridineHCID 442506525'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-phenylcarbamoyl-uridine

Product 1

HCID 668425975'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-phenylcarbamoyl-uridine

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

The THF solution (2 ml) including 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.05 mmol, 15.2 mg) and copper chloride (II) (0.05 mmol, 6.9 mg) was stirred for a day at room temperature. After the reaction mixture was cooled to 0° C., the THF solution (2 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.5 mmol, 274 mg) and the THF solution (2 ml) of phenyl isocyanate (0.5 mmol, 59.6 mg) are added thereto. After the mixture was continuously stirred for two hours at 0° C., 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 94:6, and the transformation ratio of the reaction was not less than 99%.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringAfter the mixture was continuously stirred for two hours at 0° C.

Sources & evidence

ORD record
ord-92063d716757447a8f2417888275b4de
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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