Sodium Hydroxide → Alendronic Acid

HRID 871804

Reaction equation

HRID 871804 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+].O.O.O.O.O.O.O.O.O.O.[O-:29][P:30]([O:33][P:34]([O-:37])([O-:36])=[O:35])(=[O:32])[O-:31].[Na+].[Na+].[Na+].[Na+].O.O.[Cl-].[Ca+2].[Cl-].C(CN)CC(P(O)(O)=O)(P(O)(O)=O)O.[O-]P(OP([O-])([O-])=O)(=O)[O-].[Cl-].[Ca+2].[Cl-].[OH-].[Na+]>O>[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].[O-:31][P:30]([O:33][P:34]([O-:37])([O-:36])=[O:35])(=[O:29])[O-:32]

Participants

9

Reactant 6

HCID 14798Sodium HydroxideHCID 3084150Sodium pyrophosphate decahydrateHCID 5284359Calcium Chloride2×HCID 6093260Calcium chloride, dihydrateHCID 23681107Alendronate SodiumHCID 131732545Alendronate pyrophosphate2×

Product 2

HCID 2088Alendronic AcidHCID 644102Pyrophosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

0.81 g sodium alendronate trihydrate and 1.12 g sodium pyrophosphate decahydrate (Na4P2O7.10 H2O) were dissolved in 75 mL water. 1.21 g calcium chloride dihydrate was dissolved in 75 mL water. The temperature of the alendronate-pyrophosphate solution was brought to 40 to 50° C. Calcium chloride and sodium hydroxide solutions were simultaneously added to the alendronate-pyrophosphate solution while stirring to keep the pH at 7.4 until all the calcium chloride solution was added. The mixture was cooled to room temperature. The precipitate was collected by filtration and washed with water. The solid was dried in an oven at 105° C. overnight. 1.06 g of calcium complex salt of alendronate with pyrophosphate was thus obtained with a molecular ratio of 1:1.

Workup

  1. customwas brought to 40 to 50° C
  2. additionwas added
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customThe solid was dried in an oven at 105° C. overnight

Sources & evidence

ORD record
ord-3896abd22b354ab4b99336e731893355
Source dataset
uspto-grants-2015_03
Patent number
US08974801B2

Linked notes

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