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

HRID 889772Notes

Reaction equation

HRID 889772 reaction equation
C(C1OC[C@H](C(C)(C)C)N=1)C1OC[C@H](C(C)(C)C)N=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:52]2[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:29][CH2:30][C@H:31]2[O:35][C@@H:34]([N:36]3[CH:43]=[CH:42][C:40](=[O:41])[NH:39][C:37]3=[O:38])[C@H:33]([OH:44])[C@@H:32]2[OH:45])=[CH:24][CH:23]=1.[C:60]1([N:66]=[C:67]=[O:68])[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=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>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([C:52]2[CH:53]=[CH:54][C:55]([O:58][CH3:59])=[CH:56][CH:57]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:29][CH2:30][C@H:31]2[O:35][C@@H:34]([N:36]3[CH:43]=[CH:42][C:40](=[O:41])[NH:39][C:37]3=[O:38])[C@H:33]([OH:44])[C@@H:32]2[O:45][C:67](=[O:68])[NH:66][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 7672Phenyl isocyanateHCID 688205Bis((S)-4-(tert-butyl)-4,5-dihydrooxazol-2-yl)methaneHCID 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′-methylenebis[(4S)-4-tert-butyl-2-oxazoline] (0.02 mmol, 5.4 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 65:35, and the transformation ratio of the reaction was 89%.

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-2e7d3f15e3434eefbc1475ed272d3a2c
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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