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

HRID 889768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889768
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:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[CH:46]=[CH:45][C:43](=[O:44])[NH:42][C:40]3=[O:41])[C@H:36]([OH:47])[C@@H:35]2[OH:48])=[CH:27][CH:26]=1.[C:63]1([N:69]=[C:70]=[O:71])[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=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>[Cu](Cl)Cl.C1COCC1>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]([C:55]2[CH:56]=[CH:57][C:58]([O:61][CH3:62])=[CH:59][CH:60]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:32][CH2:33][C@H:34]2[O:38][C@@H:37]([N:39]3[CH:46]=[CH:45][C:43](=[O:44])[NH:42][C:40]3=[O:41])[C@H:36]([OH:47])[C@@H:35]2[O:48][C:70](=[O:71])[NH:69][C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 7672Phenyl isocyanateHCID 688211(S,S)-2,6-Bis(4-isopropyl-2-oxazolin-2-yl)pyridineHCID 117633095'-O-(Bis(4-methoxyphenyl)phenylmethyl)uridineHCID 442506525'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-O-phenylcarbamoyl-uridine

Produkt 1

HCID 668425975'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-phenylcarbamoyl-uridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

The THF solution (1.5 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.03 mmol, 9.1 mg) and copper chloride (II) (0.03 mmol, 4.1 mg) was stirred for one day at room temperature. After the reaction mixture was cooled to −30° C., the THF solution (1.5 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.3 mmol, 164.3 mg) and the THF solution (1.5 ml) of phenyl isocyanate (0.3 mmol, 35.8 mg) were added thereto. After the mixture was continuously stirred for two hours at −30° C., 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 97:3, and the transformation ratio of the reaction was not less than 99%.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to −30° C.
  2. stirringAfter the mixture was continuously stirred for two hours at −30° C.

Quellen und Nachweise

ORD-Eintrag
ord-6dfbc551e4694c47b6606f71616a6091
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252919B2

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