Sulfuric Acid → Xylostasin

HRID 437262Notes

Reaction equation

HRID 437262 reaction equation
S(=O)(=O)(O)O.[CH2:6]1[C@@H:11]([NH:12]C([C@@H](O)CCN)=O)[C@H:10]([OH:20])[C@@H:9]([O:21][C@@H:22]2[O:26][C@H:25]([CH2:27][OH:28])[C@H:24]([OH:29])[C@H:23]2[OH:30])[C@H:8]([O:31][C@H:32]2[O:37][C@H:36]([CH2:38][NH2:39])[C@@H:35]([OH:40])[C@H:34]([OH:41])[C@H:33]2[NH2:42])[C@H:7]1[NH2:43]>[OH-].[Ba+2].[OH-]>[CH2:6]1[C@H:7]([NH2:43])[C@@H:8]([O:31][C@H:32]2[O:37][C@H:36]([CH2:38][NH2:39])[C@@H:35]([OH:40])[C@H:34]([OH:41])[C@H:33]2[NH2:42])[C@H:9]([O:21][C@@H:22]2[O:26][C@H:25]([CH2:27][OH:28])[C@H:24]([OH:29])[C@H:23]2[OH:30])[C@@H:10]([OH:20])[C@@H:11]1[NH2:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12302171Butirosin A

Product 1

HCID 73079Xylostasin

Reagents, catalysts & solvents 1

HCID 6093286Barium hydroxideSolvent

Procedure

In 250 parts by volume of an 0.5N aqueous solution of barium hydroxide is dissolved 5.0 parts of butirosin A. The solution is refluxed for 2 hours and then cooled. The solution is neutralized with 1 N sulfuric acid. The resulting precipitate of barium sulfate is removed off by centrifuge. The supernatant fluid is run onto a colume of 300 parts by volume of cation exchange resin (Amberlite CG-50(NH4 +-form) (Rohm and Haas Co.)). The colume is washed with water and eluted with 0.2 N aqueous ammonia. Fractions containing xylostasin which is detected by thin layer chromatography are pooled and concentrated under reduced pressure to dryness and lyophilized, whereby 3.8 parts of xylostasin as white powders are obtained.

Workup

  1. temperatureThe solution is refluxed for 2 hours
  2. temperaturecooled
  3. customThe resulting precipitate of barium sulfate is removed off by centrifuge
  4. washThe colume is washed with water
  5. washeluted with 0.2 N aqueous ammonia
  6. additionFractions containing xylostasin which
  7. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-7e17ae40e3274a2dabdb7be6ec73ee50
Source dataset
uspto-grants-1977_06
Patent number
US04029883

Reaction notes

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