Reacción #1350596

Ecuación de reacción

neomycin sulfate

HBr

→

2-deoxystreptamine hydrobromide

Rendimiento 61.0%

2-Deoxystreptamine Hydrobromide

Rendimiento 61.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe solution is concentrated to dryness at 60° C. under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue is dissolved into water (H2O) (100 mL), and activated charcoal (10 g)
3. 3
   workup.ADDITIONis added
4. 4
   Otrothe charcoal is removed by filtration through Celite
5. 5
   Concentraciónthe solution is concentrated to a syrup
6. 6
   workup.ADDITIONMethanol (100 mL) is added
7. 7
   workup.STIRRINGthe mixture is stirred for 2 hours t room temperature
8. 8
   FiltraciónThe solid product is filtered

Procedimiento

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.

Fuente