Lithium Hydroxide → HCID 54429635, Verbindung

HRID 1281673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281673
[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([O:19]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([CH3:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.[Li+].[OH-].BrC1N([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)C2C=C(Cl)C(Cl)=CC=2N=1>O1CCOCC1>[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@@H:18]([OH:19])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[C:26]([CH3:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 30063172-bromo-5,6-dichloro-1-beta-D-ribopyranosyl-1H-benzimidazoleHCID 53855313HCID 53855313, Verbindung

Produkt 1

HCID 54429635HCID 54429635, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Bromo-5-chloro-6-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.097 g ) was deprotected as outlined in General Procedure V by being dissolved in 5 ml dioxane and the resultant solution cooled in an ice bath between 0 and 5° C. To this solution was added all at once, 0.78 ml (0.78 mmol) of 1M aq. LiOH. The mixture was removed from the ice bath and allowed to stir at ambient temperature for 0.5 h. The mixture was diluted with 50 ml of pH 7 phosphate buffer and extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate (anhyd.), filtered and solvents evaporated. The residue was triturated in dichloromethane and 0.028 g (0.074 mmol) of 2-bromo-5,6-dichloro-1-beta-D-ribopyranosyl-1H-benzimidazole was collected by vacuum filtration. The product was dried in a vacuum oven at 50° C. overnight; m.p. 150° C. (foams); MS (AP+): m/z (rel. intensity) 400 (1.0, M+23 (Na)); 1H NMR (DMSO-d6) δ7.67 (s,1H), 7.65 (s, 1H), 5.62-5.60 (d, J=8.9 Hz), 5.13 (bs, 2H), 4.88-4.87 (m, 1H), 4.13 (bs, 1H), 4.00 (bs, 2H), 3.93 (m, 1H), 2.40 (s, 3H).

Aufarbeitung

  1. customThe mixture was removed from the ice bath
  2. additionThe mixture was diluted with 50 ml of pH 7 phosphate buffer
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over magnesium sulfate (anhyd.)
  5. filtrationfiltered
  6. customsolvents evaporated
  7. customThe residue was triturated in dichloromethane
  8. customThe product was dried in a vacuum oven at 50° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-47b9bd75412440e3b5d89272ad137f15
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455507B1

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