Ethanolamine → HCID 54257974, compound
Reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Br[C:6]1[N:10]([C@H:11]2[O:23][C@@H:22]([CH2:24][O:25]C(=O)C)[C@H:17]([O:18]C(=O)C)[C@@H:12]2[O:13]C(=O)C)[C:9]2[CH:29]=[C:30]([Cl:34])[C:31]([Cl:33])=[CH:32][C:8]=2[N:7]=1.C(O)C.CCOCC>CN(C=O)C.C(OCC)(=O)C>[Cl:33][C:31]1[C:30]([Cl:34])=[CH:29][C:9]2[N:10]([C@H:11]3[O:23][C@@H:22]([CH2:24][OH:25])[C@H:17]([OH:18])[C@@H:12]3[OH:13])[C:6]([NH:4][CH2:3][CH2:1][OH:2])=[N:7][C:8]=2[CH:32]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Ethanolamine (25 ml) and 2-bromo-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (0.62 g, 1.2 mmol) were combined with absolute ethanol (50 mL) and stirred at 80° C. for 24 h. The reaction mixture was concentrated and purified on a silica gel column (2.5 cm×16 cm, 230-400 mesh) with 1:20 methanol:dichloromethane (500 mL), then 1:9 methanol:dichloromethane. Crude product was obtained which was ether purified on a silica gel filter pad with 1:1 acetone: dichloromethane and then with 1:2 ethanol:dichloromethane. Further purification on a chromatotron fitted with a 2 mm rotor, using 1:6 ethanol:ethyl acetate provided pure product (0.064 g, 0.17 mmol, 14%); [a]20D=(−) 14.2 (c=0.5 DMF).
Workup
- concentrationThe reaction mixture was concentrated
- custompurified on a silica gel column (2.5 cm×16 cm, 230-400 mesh) with 1:20 methanol
- customCrude product was obtained which
- custompurified on a silica gel
- filtrationfilter pad with 1:1 acetone
- customFurther purification on a chromatotron
- customfitted with a 2 mm rotor
Sources & evidence
- ORD record
- ord-11155b802022450caae629f1e27cdf00
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06307043B1
Reaction notes
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