Ethyl Acetate → 1-[(Diethylphosphonomethoxy)methoxymethyl]thymine

HRID 1551

Reaktionsgleichung

Reaktionsgleichung von HRID 1551
[C:1]([O:9][CH2:10][O:11][CH2:12][N:13]1[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]1=[O:15])(=O)C1C=CC=CC=1.C([CH:24]([CH2:30]C)[O:25][P:26]([OH:29])([OH:28])=O)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:44](OCC)(=O)[CH3:45]>C1C=CC=CC=1>[CH2:44]([O:29][P:26]([CH2:1][O:9][CH2:10][O:11][CH2:12][N:13]1[CH:21]=[C:19]([CH3:20])[C:17](=[O:18])[NH:16][C:14]1=[O:15])([O:25][CH2:24][CH3:30])=[O:28])[CH3:45]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 65367Trimethylsilyl triflateHCID 148435351-[(Benzoyloxy)methoxymethyl]thymineHCID 54112757Pentan-3-yl dihydrogen phosphate

Produkt 1

HCID 148865321-[(Diethylphosphonomethoxy)methoxymethyl]thymine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 1-[(benzoyloxy)methoxymethyl]thymine (2.9 g, 10 mmol) and diethyl phosphonomethanol (1.85 g, 11 mmol) in benzene (180 mL) was added trimethylsilyl trifluoromethanesulfonate (0.05 mL) via a syringe under nitrogen. The solution was heated at 85° C. for 20 min. After cooling to room temperature, ethyl acetate (50 mL) was added and washed with aqueous bicarbonate, brine dried (MgSO4), filtered and concentrated in vacuo. The resultant yellow oil was purified by silica gel column chromatography using CH2Cl2 /5% MeOH as an eluent to give the title compound as a white oil: yield 980 mg (30%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous bicarbonate, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant yellow oil was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-32e98db4036848ce8b8264c0ec0c3131
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726174

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