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 614456Notes

Reaction equation

HRID 614456 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-].[Na+].[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

5

Reactant 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 6093286Barium hydroxide2×HCID 101316942HCID 101316942, compound2×

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

Procedure

Fortimicin KE may also be obtained by heating Fortimicin D in an alkaline aqueous solution such as sodium hydroxide and barium hydroxide. Specifically, Fortimicin D is heated in an aqueous solution of saturated barium hydroxide at a temperature of 100° C. for 3 hours. Then the reaction solution is neutralized with dry ice and the resulting precipitate of barium carbonate is removed by filtration. The filtrate is concentrated and passed through a column packed with Amberlite CG-50 (ammonium form). After washing the column with water, elution is carried out with 0.2N aqueous ammonia. First, a small amount of reaction by-products is eluted and subsequently Fortimicin KE is eluted. The fractions containing Fortimicin KE are combined and concentrated under reduced pressure. The concentrate is then freeze-dried to obtain the free base of Fortimicin KE.

Workup

  1. customthe resulting precipitate of barium carbonate is removed by filtration
  2. concentrationThe filtrate is concentrated
  3. washAfter washing the column
  4. washwith water, elution
  5. customFirst, a small amount of reaction by-products
  6. washis eluted
  7. washsubsequently Fortimicin KE is eluted
  8. additionThe fractions containing Fortimicin KE
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrate is then freeze-dried

Sources & evidence

ORD record
ord-6768d87d0532461fb90e6b08b1d13719
Source dataset
uspto-grants-1979_03
Patent number
US04145253

Reaction notes

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