Carbon Dioxide → 4-Amino-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl)-6-O-methyl-1-(methylamino)-L-chiro-inositol

HRID 1855792Notes

Reaction equation

HRID 1855792 reaction equation
[CH3:1][N:2](C(CN)=O)[C@@H:3]1[C@@H:8]([O:9][CH3:10])[C@@H:7]([OH:11])[C@H:6]([NH2:12])[C@@H:5]([O:13][C@H:14]2[O:19][C@H:18]([CH2:20][NH2:21])[CH2:17][CH2:16][C@H:15]2[NH2:22])[C@@H:4]1[OH:23].[OH-].[Ba+2].[OH-].C(=O)=O>>[CH3:1][NH:2][C@@H:3]1[C@@H:8]([O:9][CH3:10])[C@@H:7]([OH:11])[C@H:6]([NH2:12])[C@@H:5]([O:13][C@H:14]2[O:19][C@H:18]([CH2:20][NH2:21])[CH2:17][CH2:16][C@H:15]2[NH2:22])[C@@H:4]1[OH:23]

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 6093286Barium hydroxideHCID 101316942HCID 101316942, compound

Product 1

HCID 1012811534-Amino-1,4-dideoxy-3-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl)-6-O-methyl-1-(methylamino)-L-chiro-inositol

Conditions

Temperature
100 °C

Procedure

In this example, 10 g of the free base of Fortimicin D is dissolved in 500 ml of aqueous solution of saturated barium hydroxide. The solution is heated at a temperature of 100° C. for 3 hours and thereafter is allowed to stand until it is cooled to room temperature. The solution is neutralized with dry ice to precipitate the barium carbonate out. Filtration is carried out to remove the precipitate and the precipitate is washed with a small amount of water. The filtrate and the washings are combined and concentrated to about 20 ml. The concentrate is passed through a column packed with 500 ml of a cation exchange resin, Amberlite CG-50 (ammonium form). After the resin is washed with water, elution is carried out with 0.2 N aqueous ammonia. The eluate is recovered in 20 ml fractions and each of the fractions is subjected to determination of activity by the paper disc method. First, a small amount of reaction by-products is eluted. Thereafter, Fortimicin KE is eluted. Active fractions are subjected to thin layer chromatography and the fractions containing Fortimicin KE are combined and concentrated under reduced pressure to 20 ml. The concentrate is freeze-dried to obtain 7.8 g of the purified preparate of the free base of Fortimicin KE, the activity of which is about 970 unit/mg.

Workup

  1. temperatureis cooled to room temperature
  2. customto precipitate the barium carbonate out
  3. filtrationFiltration
  4. customto remove the precipitate
  5. washthe precipitate is washed with a small amount of water
  6. concentrationconcentrated to about 20 ml
  7. washAfter the resin is washed with water, elution
  8. customThe eluate is recovered in 20 ml fractions
  9. customFirst, a small amount of reaction by-products
  10. washis eluted
  11. washThereafter, Fortimicin KE is eluted
  12. additionthe fractions containing Fortimicin KE
  13. concentrationconcentrated under reduced pressure to 20 ml
  14. customThe concentrate is freeze-dried

Sources & evidence

ORD record
ord-cfc9830613bb4f1082b8793dee860038
Source dataset
uspto-grants-1980_08
Patent number
US04216308

Reaction notes

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