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

HRID 366951

Reaktionsgleichung

Reaktionsgleichung von HRID 366951
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) δ 2.24 (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-6b7327d5e5d44872a97dd8c20ccae581
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130326

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