Methane → Siseptin

HRID 1758030

Reaction equation

HRID 1758030 reaction equation
[CH3:1][C@@:2]1([OH:31])[C@H:7]([NH:8][CH3:9])[C@@H:6]([OH:10])[C@@H:5]([O:11][C@@H:12]2[C@@H:17]([OH:18])[C@H:16]([O:19][C@H:20]3[O:25][C:24]([CH2:26][NH2:27])=[CH:23][CH2:22][C@H:21]3[NH2:28])[C@@H:15]([NH2:29])[CH2:14][C@H:13]2[NH2:30])[O:4][CH2:3]1.C.[S:33](=[O:37])(=[O:36])([OH:35])[OH:34]>O>[CH3:1][C@@:2]1([OH:31])[C@H:7]([NH:8][CH3:9])[C@@H:6]([OH:10])[C@@H:5]([O:11][C@@H:12]2[C@@H:17]([OH:18])[C@H:16]([O:19][C@H:20]3[O:25][C:24]([CH2:26][NH2:27])=[CH:23][CH2:22][C@H:21]3[NH2:28])[C@@H:15]([NH2:29])[CH2:14][C@H:13]2[NH2:30])[O:4][CH2:3]1.[OH:36][S:33]([OH:37])(=[O:35])=[O:34]

Participants

5

Reactant 3

HCID 297MethaneHCID 1118Sulfuric AcidHCID 36119Sisomicin

Product 1

HCID 65334Siseptin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 g of the pure sisomicin base are dissolved in 60 ml of ion free water and to that solution as much 5 N sulfuric acid solution is added dropwise, as in needed to obtain a level of pH 4.3. Thereafter 1.5 g of active charcoal are added to the solution and the mixture is stirred for 30 minutes, then filtered on Seitz sheet. The filter is washed with 3×50 ml of ion free water and the unified filtrate is added by continuous stirring to 1 liter of methanol. The solution containing separated precipitate is allowed to stand in a cooling room, whereafter the precipitate is filtered out. The filtered sisomicin sulfate is washed with 3×50 ml of methanol, and dried in vacuum at 50° C. above P2O5 to constant weight. Thus 22 g of sisomicin sulfate are obtained.

Workup

  1. additionis added dropwise
  2. customto obtain a level of pH 4.3
  3. filtrationfiltered on Seitz sheet
  4. washThe filter is washed with 3×50 ml of ion free water
  5. additionthe unified filtrate is added
  6. stirringby continuous stirring to 1 liter of methanol
  7. additionThe solution containing
  8. customseparated precipitate
  9. filtrationis filtered out
  10. washThe filtered sisomicin sulfate is washed with 3×50 ml of methanol
  11. dry with materialdried in vacuum at 50° C. above P2O5 to constant weight

Sources & evidence

ORD record
ord-36c33ab71acb480698a94503210b25c8
Source dataset
uspto-grants-1983_02
Patent number
US04371622

Linked notes

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