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

HRID 889770Notes

Reaction equation

HRID 889770 reaction equation
C(C1OC[C@H](C(C)(C)C)N=1)(C1OC[C@H](C(C)(C)C)N=1)(C)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:31][CH2:32][C@H:33]2[O:37][C@@H:36]([N:38]3[CH:45]=[CH:44][C:42](=[O:43])[NH:41][C:39]3=[O:40])[C@H:35]([OH:46])[C@@H:34]2[OH:47])=[CH:26][CH:25]=1.[C:62]1([N:68]=[C:69]=[O:70])[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=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>[CH3:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([C:54]2[CH:55]=[CH:56][C:57]([O:60][CH3:61])=[CH:58][CH:59]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:31][CH2:32][C@H:33]2[O:37][C@@H:36]([N:38]3[CH:45]=[CH:44][C:42](=[O:43])[NH:41][C:39]3=[O:40])[C@H:35]([OH:46])[C@@H:34]2[O:47][C:69](=[O:70])[NH:68][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 7672Phenyl isocyanateHCID 688208t-Bu-box, (S,S)-HCID 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 2,2′-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%.

Workup

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

Sources & evidence

ORD record
ord-aff814f891ab465cb6ee2f8f5384fb81
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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