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

HRID 889771Notes

Reaction equation

HRID 889771 reaction equation
C1OC(C2OCC(CC3C=CC=CC=3)N=2)=NC1CC1C=CC=CC=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:34][CH2:35][C@H:36]2[O:40][C@@H:39]([N:41]3[CH:48]=[CH:47][C:45](=[O:46])[NH:44][C:42]3=[O:43])[C@H:38]([OH:49])[C@@H:37]2[OH:50])=[CH:29][CH:28]=1.[C:65]1([N:71]=[C:72]=[O:73])[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=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>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]([C:57]2[CH:58]=[CH:59][C:60]([O:63][CH3:64])=[CH:61][CH:62]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:34][CH2:35][C@H:36]2[O:40][C@@H:39]([N:41]3[CH:48]=[CH:47][C:45](=[O:46])[NH:44][C:42]3=[O:43])[C@H:38]([OH:49])[C@@H:37]2[O:50][C:72](=[O:73])[NH:71][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 7672Phenyl isocyanateHCID 37824184,4'-DiBenzyl-4,4',5,5'-tetrahydro-2,2'-bioxazoleHCID 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′-bis[(4S)-4-benzyl-2-oxazoline] (0.02 mmol, 6.5 mg) and Cu(OTf)2 (II) (0.02 mmol, 7.2 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 (0.2 mmol, 109 mg) and the 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 overnight 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 70:30, and the transformation ratio of the reaction was 83%.

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 overnight at room temperature

Sources & evidence

ORD record
ord-d0e940c2040f41e480a5e2a29990dcec
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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