氢溴酸 → HCID 178419707，化合物

HRID 1263414

反应方程式

HRID 1263414 反应方程式
[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]

参与物

3

反应物 2

HCID 260氢溴酸HCID 197162neomycin B sulphate

产物 1

HCID 178419707HCID 178419707，化合物收率 61%

反应条件

温度
100 °C

实验过程

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.

后处理

  1. concentrationThe solution is concentrated to dryness at 60° C. under reduced pressure
  2. dissolutionThe residue is dissolved into water (H2O) (100 mL), and activated charcoal (10 g)
  3. additionis added
  4. customthe charcoal is removed by filtration through Celite
  5. concentrationthe solution is concentrated to a syrup
  6. additionMethanol (100 mL) is added
  7. stirringthe mixture is stirred for 2 hours t room temperature
  8. filtrationThe solid product is filtered

来源与证据

ORD记录
ord-be16453c17f04decb0a2e70f13ec9665
来源数据集
uspto-grants-2003_04
专利号
US06541456B1

关联笔记

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