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

HRID 889776Notes

Reaction equation

HRID 889776 reaction equation
C1([C@H]2COC(C3C=CC=C(C4OC[C@H](C5C=CC=CC=5)N=4)N=3)=N2)C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[O:38][CH2:39][C@H:40]2[O:44][C@@H:43]([N:45]3[CH:52]=[CH:51][C:49](=[O:50])[NH:48][C:46]3=[O:47])[C@H:42]([OH:53])[C@@H:41]2[OH:54])=[CH:33][CH:32]=1.[C:69]1([N:75]=[C:76]=[O:77])[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=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>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2].C1COCC1>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([C:61]2[CH:62]=[CH:63][C:64]([O:67][CH3:68])=[CH:65][CH:66]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[O:38][CH2:39][C@H:40]2[O:44][C@@H:43]([N:45]3[CH:52]=[CH:51][C:49](=[O:50])[NH:48][C:46]3=[O:47])[C@H:42]([OH:53])[C@@H:41]2[O:54][C:76](=[O:77])[NH:75][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 7672Phenyl isocyanateHCID 70101002,6-Bis(4S)(4-phenyl-4,5-dihydro-1,3-oxazol-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 2734996copper(II) trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

The THF solution (1 ml) containing 2,6-bis[(4S)-phenyl-2-oxazoline-2-yl]pyridine (0.03 mmol, 11.1 mg) and Cu(OTf)2 (II) (0.03 mmol, 11.1 mg) was stirred for 30 minutes at room temperature. After the reaction mixture was cooled to 0° C., the THF solution (1.5 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.3 mmol, 164.0 mg) and the THF solution (1 ml) of phenyl isocyanate (0.3 mmol, 35.7 mg) were added thereto. After the mixture was continuously stirred for 19 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 68:32, and the transformation ratio of the reaction was 81%.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringAfter the mixture was continuously stirred for 19 hours at 0° C.

Sources & evidence

ORD record
ord-d1dffcf3765a4e078eb6603fd86bf9ca
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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