Isopropanol → 1-beta-L-Ribofuranosyl-6-methyluracil

HRID 1368716

Reaktionsgleichung

Reaktionsgleichung von HRID 1368716
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[C:41]([CH3:42])=[CH:40][C:38](=[O:39])[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1.CC(O)C>N>[C@H:11]1([N:34]2[C:41]([CH3:42])=[CH:40][C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

Komponenten

4

Edukt 2

HCID 3776IsopropanolHCID 120432031-(2',3',5'-Tri-O-benzoyl-beta-L-ribofuranosyl)-6-methyluracil

Produkt 1

HCID 543042731-beta-L-Ribofuranosyl-6-methyluracil

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel

Versuchsvorschrift

A solution of 40 (4.50 g, 7.86 mmol) was dissolved in sat. methanolic ammonia (60 mL). The reaction mixture was heated at 100° C. for 17 h in a steel bomb. The reaction vessel was cooled to room temperature and concentrated to yield an oil. The reside was further purified by silica gel flash column chromatography using dichloromethane and methanol (9:1) as the eluent. Pure fractions were collected and evaporated to give a white solid. This was further recyrstallized from 2-propanol to afford 1.98 g (94%) of pure 41: mp 175-177° C.; 1H NMR (Me2SO-d6) δ2.24 (s, 3H, CH3), 3.42-3.57 (m, 2H, C5′H), 3.68 (m, 1H, C4′H), 4.0 (m, 1H, C3′H), 4.53 (m, 1H, C2′H), 4.68, 4.94, 5.22 (m, 3H, 3 OH, D2O exchangeable), 5.43 (d, 1H, C1′H, J1′,2′=3.85 Hz), 5.56 (s, 1H, C5H) and 11.25 (s, 1H, NH). Anal. Calc. for C10H14N2O6 (258.23): C, 46.51; H, 5.46; N, 10.85. Found: C, 46.66; H, 5.26; N, 10.66

Aufarbeitung

  1. concentrationconcentrated
  2. customto yield an oil
  3. customThe reside was further purified by silica gel flash column chromatography
  4. customPure fractions were collected
  5. customevaporated
  6. customto give a white solid
  7. customto afford 1.98 g (94%) of pure 41

Quellen und Nachweise

ORD-Eintrag
ord-79ae95b65e0c4876afd3e9c9094dca34
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573248B2

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