Methanol → 5,6-Dichloro-1-(2-deoxy-2-fluoro-3,5-diacetyl-beta-D-ribofuranosyl)benzimidazole
Reaction equation
[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]2[N:6]([C@@H:9]3[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:10]3[F:17])[CH:7]=[N:8][C:4]=2[CH:3]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C[OH:29].N1[CH:35]=[CH:34]C=CC=1>>[Cl:1][C:2]1[C:19]([Cl:20])=[CH:18][C:5]2[N:6]([C@@H:9]3[O:14][C@H:13]([CH:15]([C:21](=[O:23])[CH3:22])[OH:16])[C@@:11]([C:34](=[O:29])[CH3:35])([OH:12])[C@H:10]3[F:17])[CH:7]=[N:8][C:4]=2[CH:3]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Compound 15 (0.45 g, 1.4 mmol) was dissolved in pyridine (20 mL) and boiled to remove water. The solution was chilled to 0° C. in an ice bath. Acetic anhydride (260 μL, 2.9 mmol, 2 equiv.) was added and the reaction mixture was allowed to warm to room temperature while stirring overnight. Methanol (3 mL) was added and the solvents removed in vacuo. Residual pyridine was removed by coevaporation with toluene (3×). The residue was partitioned between water and the ethyl acetate. The ethyl acetate solution was dried with magnesium sulfate, filtered, and the solvent removed in vacuo to yield 0.56 g (98%) of compound 16. The product was used without further purification.
Workup
- customto remove water
- temperatureto warm to room temperature
- customthe solvents removed in vacuo
- customResidual pyridine was removed by coevaporation with toluene (3×)
- customThe residue was partitioned between water
- dry with materialThe ethyl acetate solution was dried with magnesium sulfate
- filtrationfiltered
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-9a97f5a9f3564ec7bc7ac5a6b666c4ad
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840743
Reaction notes
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