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

HRID 889773Notes

Reaction equation

HRID 889773 reaction equation
C(C1OC[C@H](C2C=CC=CC=2)N=1)(C1OC[C@H](C2C=CC=CC=2)N=1)(C)C.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([C:58]2[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:35][CH2:36][C@H:37]2[O:41][C@@H:40]([N:42]3[CH:49]=[CH:48][C:46](=[O:47])[NH:45][C:43]3=[O:44])[C@H:39]([OH:50])[C@@H:38]2[OH:51])=[CH:30][CH:29]=1.[C:66]1([N:72]=[C:73]=[O:74])[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=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>[CH3:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([C:58]2[CH:59]=[CH:60][C:61]([O:64][CH3:65])=[CH:62][CH:63]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[O:35][CH2:36][C@H:37]2[O:41][C@@H:40]([N:42]3[CH:49]=[CH:48][C:46](=[O:47])[NH:45][C:43]3=[O:44])[C@H:39]([OH:50])[C@@H:38]2[O:51][C:73](=[O:74])[NH:72][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 7672Phenyl isocyanateHCID 676388(S,S)-2,2'-Isopropylidenebis(4-phenyl-2-oxazoline)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-phenyl-2-oxazoline] (0.02 mmol, 7.2 mg) and Cu(OTf)2 (II) (0.02 mmol, 6.7 mg) was stirred for 30 minutes at room temperature. After the reaction mixture was cooled to 0° C., THF solution (1 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.2 mmol, 109.3 mg) and THF solution (1 ml) of phenyl isocyanate (0.2 mmol, 23.8 mg) were added thereto. After the mixture was continuously stirred for 1 hour at 0° C. and 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]-2′-O-phenylcarbamoyl-uridine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-3′-O-phenylcarbamoyl-uridine were produced at the ratio of 60:40, and the transformation ratio of the reaction was 96%.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringAfter the mixture was continuously stirred for 1 hour at 0° C. and for 4 hours at room temperature

Sources & evidence

ORD record
ord-59bf2ec771a2403cbd47184e7f25f698
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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