Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3'-O-phenylcarbamoyladenosine

HRID 889777Notes

Reaction equation

HRID 889777 reaction equation
C([C@H]1COC(C2C=CC=C(C3OC[C@H](C(C)C)N=3)N=2)=N1)(C)C.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:65]2[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=2)([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[C:56]4[N:55]=[CH:54][N:53]=[C:43]([NH:44][C:45](=[O:52])[C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[C:42]=4[N:41]=[CH:40]3)[C@H:36]([OH:57])[C@@H:35]2[OH:58])=[CH:27][CH:26]=1.[C:73]1([N:79]=[C:80]=[O:81])[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.C([O-])([O-])=O.[K+].[K+].COC1C=CC(C(C2C=CC(OC)=CC=2)(C2C=CC=CC=2)OC[C@H]2O[C@@H](N3C4N=CN=C(NC(=O)C5C=CC=CC=5)C=4N=C3)[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>[CH3:72][O:71][C:68]1[CH:67]=[CH:66][C:65]([C:31]([C:28]2[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2)([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[C:56]4[N:55]=[CH:54][N:53]=[C:43]([NH:44][C:45](=[O:52])[C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[C:42]=4[N:41]=[CH:40]3)[C@H:36]([OH:57])[C@@H:35]2[O:58][C:80](=[O:81])[NH:79][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)=[CH:70][CH:69]=1

Participants

8

Reactant 5

HCID 7672Phenyl isocyanateHCID 11430Potassium CarbonateHCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridineHCID 142821355'-DMT-Bz-rAHCID 668426065'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-2'-O-phenylcarbamoyladenosine

Product 1

HCID 668427225'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3'-O-phenylcarbamoyladenosine

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

The THF solution (75 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.15 mmol, 45.2 mg) and copper chloride (II) (0.15 mmol, 25.6 mg) was stirred for a day at room temperature. After the reaction mixture was cooled to −15° C., the THF solution (15 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyladenosine (1.5 mmol, 1.0 g) and the THF solution (15 ml) of phenyl isocyanate (1.5 mmol, 178.7 mg) and K2CO3 (1.5 mmol, 207.3 mg) were added thereto. After the mixture was continuously stirred for 42 hours at −15° C., the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-2′-O-phenylcarbamoyladenosine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3′-O-phenylcarbamoyladenosine were produced at the ratio of 93:7, and the transformation ratio of the reaction was 99%.

Workup

  1. temperatureAfter the reaction mixture was cooled to −15° C.
  2. stirringAfter the mixture was continuously stirred for 42 hours at −15° C.

Sources & evidence

ORD record
ord-ae90ea5387c9477da37e95858a7ff07b
Source dataset
uspto-grants-2012_08
Patent number
US08252919B2

Reaction notes

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