Hydrogen Bromide → HCID 178419707, compound
Reaction equation
[CH2:1]1[C@H:6]([NH2:7])[C@@H:5]([O:8][C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2N)[C@H:4]([O:20][C@@H]2O[C@H](CO)[C@@H](O[C@H]3O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@H]2O)[C@@H:3]([OH:41])[C@@H:2]1[NH2:42].OS(O)(=O)=O.[BrH:48]>>[CH2:1]1[C@H:2]([NH2:42])[C@@H:3]([OH:41])[C@H:4]([OH:20])[C@@H:5]([OH:8])[C@@H:6]1[NH2:7].[BrH:48]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A solution of neomycin sulfate (20 g, 20.8 mmol) in HBr (150 mL, 48%) is stirred under reflux at 100° C. for 40 hours. The solution is concentrated to dryness at 60° C. under reduced pressure. The residue is dissolved into water (H2O) (100 mL), and activated charcoal (10 g) is added. After stirring at room temperature for 10 hours, the charcoal is removed by filtration through Celite, and the solution is concentrated to a syrup. Methanol (100 mL) is added and the mixture is stirred for 2 hours t room temperature. The solid product is filtered to give 2-deoxystreptamine hydrobromide 3 (4.1 g, 61%). Rf: 0.2 (CH3OH/NH4OH=4:1); 1H-NMR (D2O, 200 MHZ): d 1.95 (1H, ddd), 2.5 (1H, m), 3.2-3.6 (9H, m); 13C-NMR (D2O, 200 MHZ): d 40.0, 65.0, 87.2, 89.5. Ref. Georgiadas, M. P.; Constantinou-Kokotou, V. J. Carbohydr. Chem. 1991, 10, 739-746.