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

HRID 889776
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 889776
C1([C@H]2COC(C3C=CC=C(C4OC[C@H](C5C=CC=CC=5)N=4)N=3)=N2)C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[O:38][CH2:39][C@H:40]2[O:44][C@@H:43]([N:45]3[CH:52]=[CH:51][C:49](=[O:50])[NH:48][C:46]3=[O:47])[C@H:42]([OH:53])[C@@H:41]2[OH:54])=[CH:33][CH:32]=1.[C:69]1([N:75]=[C:76]=[O:77])[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=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>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([C:61]2[CH:62]=[CH:63][C:64]([O:67][CH3:68])=[CH:65][CH:66]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[O:38][CH2:39][C@H:40]2[O:44][C@@H:43]([N:45]3[CH:52]=[CH:51][C:49](=[O:50])[NH:48][C:46]3=[O:47])[C@H:42]([OH:53])[C@@H:41]2[O:54][C:76](=[O:77])[NH:75][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[CH:35][CH:36]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7672Phenyl isocyanateHCID 7010100(S,S)-2,6-Bis(4-phenyl-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 66842597
5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-O-phenylcarbamoyl-uridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734996copper(II) trifluoromethanesulfonateKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

The THF solution (1 ml) containing 2,6-bis[(4S)-phenyl-2-oxazoline-2-yl]pyridine (0.03 mmol, 11.1 mg) and Cu(OTf)2 (II) (0.03 mmol, 11.1 mg) was stirred for 30 minutes at room temperature. After the reaction mixture was cooled to 0° C., the THF solution (1.5 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]uridine (0.3 mmol, 164.0 mg) and the THF solution (1 ml) of phenyl isocyanate (0.3 mmol, 35.7 mg) were added thereto. After the mixture was continuously stirred for 19 hours at 0° 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 68:32, and the transformation ratio of the reaction was 81%.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringAfter the mixture was continuously stirred for 19 hours at 0° C.

Quellen und Nachweise

ORD-Eintrag
ord-d1dffcf3765a4e078eb6603fd86bf9ca
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08252919B2

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