Acetic Acid → 1-(4-Dimethylphosphonomethoxytetrahydro-2-furyl)thymine

HRID 1938796

Reaktionsgleichung

Reaktionsgleichung von HRID 1938796
CO[CH:3]1[O:7][CH:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][CH2:4]1.CO[P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20].[C:25](O)(=[O:27])C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:24][O:23][P:19]([CH2:25][O:27][CH:4]1[CH2:3][O:7][CH:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5]1)([O:21][CH3:22])=[O:20]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 10541Trimethyl PhosphateHCID 521998p-Toluenesulfonic acid monohydrateHCID 189394271-(5-Methoxytetrahydro-2-furyl)thymine

Produkt 1

HCID 540926261-(4-Dimethylphosphonomethoxytetrahydro-2-furyl)thymine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1-(5-methoxytetrahydro-2-furyl)thymine (5.2 g, 23 mmol) and dimethylphosphonomethanol (6.5 g, 44 mmol) in toluene was added acetic acid (5 mL) and p-toluenesulfonic acid monohydrate (500 mg, 2.6 mmol). The solution was heated at 100° C. for 2 hr and the resulting insoluble solid was removed by suction filtration. After removal of the solvent under reduced pressure, the residual oil was chromotographed on silica gel using CH2Cl2 /5% MeOH as eluent to give the title compound as a cis/trans mixture (6:4): yield 5.0 g (60%).

Aufarbeitung

  1. customthe resulting insoluble solid was removed by suction filtration
  2. customAfter removal of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-eb48b8fea951419ab801ead01fcbe979
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05693798

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