Methanesulfonyl chloride → 2',3',5'-Tris(methanesulfonyl)-5-methyluridine

HRID 129097

Reaktionsgleichung

Reaktionsgleichung von HRID 129097
[CH3:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH3:19][S:20]([C@@:8]1([OH:9])[C@:10]([S:20]([CH3:19])(=[O:22])=[O:21])([OH:11])[C@@H:12]([CH:13]([S:20]([CH3:19])(=[O:22])=[O:21])[OH:14])[O:15][C@H:7]1[N:6]1[CH:16]=[C:2]([CH3:1])[C:3](=[O:18])[NH:4][C:5]1=[O:17])(=[O:22])=[O:21]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 4454085-Methyluridine

Produkt 1

HCID 536894342',3',5'-Tris(methanesulfonyl)-5-methyluridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred mixture of 5-methyluridine (12.8 g, 50 mmol) in pyridine (75 mL) at 0° C. was added methanesulfonyl chloride (17.4 mL, 225 mmol). The reaction mixture was stirred at 0° C. for five hours then poured into ice-water (500 mL) with stirring. Trimethanesulfonyl-5-methyluridine (2) precipitated and the mixture was stirred for 5 min. The solid product was collected by filtration and washed with water (3×200 mL) and dried. Yield, 21.6 g, 89%.

Aufarbeitung

  1. stirringwith stirring
  2. customTrimethanesulfonyl-5-methyluridine (2) precipitated
  3. stirringthe mixture was stirred for 5 min
  4. filtrationThe solid product was collected by filtration
  5. washwashed with water (3×200 mL)
  6. customdried
  7. customYield

Quellen und Nachweise

ORD-Eintrag
ord-8a72c79e271e4490ac9e4fe591f46403
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466787

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