Ammonia → 5-Fluoro-2'-O-methyluridine

HRID 2210629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210629
C([O:9][C@@H:10]1[C@@H:14]([CH2:15][O:16]C(=O)C2C=CC=CC=2)[O:13][C@@H:12]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:11]1[O:34][CH3:35])(=O)C1C=CC=CC=1.N>CO>[CH3:35][O:34][C@@H:11]1[C@H:10]([OH:9])[C@@H:14]([CH2:15][OH:16])[O:13][C@H:12]1[N:25]1[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]1=[O:27]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 100055463',5'-Di-O-benzoyl-5-fluoro-2'-O-methyluridine

Produkt 1

HCID 217323735-Fluoro-2'-O-methyluridineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3',5'-Di-O-benzoyl-2'-O-methyl-5-fluorouridine (9.6 g, 20 mmoles) was dissolved in methanol (350 ml) which had been previously saturated with ammonia at -20° C. The solution was sealed in a stainless steel bomb at room temperature for 17 hours and then concentrated to an oil under reduced pressure. The oil was chromatographed on silica gel (200 g) using ethyl acetate to give 5.4 g (98%) of 2'-O-methyl-5-fluorouridine as a white solid. A portion (0.5 g) was crystallized from ethyl acetate/toluene to yield 0.4 g of white needles as the analytical sample, mp 151°-152° C. (lit. M. J. Robins, et. al., J. Am. Chem. Soc., 89, 7381 (1976)., mp 144°-147° C.). 1H NMR (DMSO-d6): δ 3.39 (s, 3H, OCH3), 3.5-3.7 (m, 2H, H-5'), 3.7-3.9 (m, 2H, H-3',4'), 4.13 (m, 1H, H-2'), 5.18 (d, J=6 Hz, 1H, 3'--OH), 5.35 (br t, 1H, 5'--OH), 5.81 (dd, 1H, H-1'), 8.35 (d, J=7 Hz, 1H, H-6), 11.40 (br d, 1H, N--H). Anal. Calcd for C10H13N2O6 (276.22): C, 43.48; H, 4.74; N, 10.14. Found: C, 43.56; H, 4.63; N, 10.02.

Aufarbeitung

  1. concentrationconcentrated to an oil under reduced pressure
  2. customThe oil was chromatographed on silica gel (200 g)

Quellen und Nachweise

ORD-Eintrag
ord-609fcb5709f64136b1c8d23cf9f89029
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05459243

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