Sodium Hydroxide → Phosphate

HRID 871806Notes

Reaction equation

HRID 871806 reaction equation
[CH2:1]([CH2:13][NH2:14])[CH2:2][C:3]([P:9]([O-:12])([OH:11])=[O:10])([P:5]([OH:8])([OH:7])=[O:6])[OH:4].O.O.O.[Na+].[P:19]([O-:23])([O-:22])([O-:21])=[O:20].[Na+].[Na+].[Na+].C(CN)CC(P(O)(O)=O)(P(O)(O)=O)O.P([O-])([O-])([O-])=O.[OH-].[Na+]>O.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH2:1]([CH2:13][NH2:14])[CH2:2][C:3]([P:5]([OH:7])([OH:8])=[O:6])([P:9]([OH:12])([OH:11])=[O:10])[OH:4].[P:19]([O-:23])([O-:22])([O-:21])=[O:20]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 24243Trisodium PhosphateHCID 23681107Alendronate SodiumHCID 131732546Alendronate phosphate

Product 2

HCID 1061PhosphateHCID 2088Alendronic Acid

Reagents, catalysts & solvents 3

HCID 11192Zinc AcetateCatalystHCID 2724192Zinc acetate (USP)CatalystHCID 962WaterSolvent2×

Procedure

3.25 g of sodium alendronate trihydrate and 1.42 g of dibasic sodium phosphate (anhydrous) were dissolved in 100 mL water. The solution temperature was kept at 50° C. on a hot plate. This temperature was maintained throughout the process. While stirring, a solution of 5.8 g of zinc acetate dihydrate in 50 mL of water was added to the alendronate-phosphate solution. The pH of the solution was kept at 7.4 by adding sodium hydroxide solution simultaneously until all the zinc acetate solution was added. The precipitate was collected by filtration and washed with water. The solid was then dried at 120° C. overnight. 5.28 g of zinc complex salt of alendronate and phosphate with a molecular ratio of 1:1 was thus obtained. The solubility of the API (as alendronic acid) in saline at room temperature for this complex is 2.4 mcg/mL, i.e. 0.00024%. It also has a very low solubility of the API.

Workup

  1. customwas kept at 50° C. on a hot plate
  2. temperatureThis temperature was maintained throughout the process
  3. additionwas added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customThe solid was then dried at 120° C. overnight

Sources & evidence

ORD record
ord-3ee63b391b5a466a962f7843514607a7
Source dataset
uspto-grants-2015_03
Patent number
US08974801B2

Reaction notes

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