Sodium Hydroxide → Alendronic Acid

HRID 871805Notes

Reaction equation

HRID 871805 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-:19][P:20]([O:23][P:24]([O:27][P:28]([O-:31])([O-:30])=[O:29])([O-:26])=[O:25])([O-:22])=[O:21].[Na+].[Na+].[Na+].[Na+].[Na+].O.O.[Cl-].[Ca+2].[Cl-].[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:28]([O:27][P:24]([O:23][P:20]([O-:22])([O-:21])=[O:19])([O-:26])=[O:25])([O-:30])=[O:29]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 24455Sodium Tripolyphosphate2×HCID 5284359Calcium Chloride2×HCID 6093260Calcium chloride, dihydrateHCID 23681107Alendronate Sodium

Product 2

HCID 2088Alendronic AcidHCID 3440921Triphosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.03 g sodium alendronate trihydrate (6.25 mmol) and 6.9 g sodium tripolyphosphate, Na5P3O10 were added to 100 mL water, and the mixture was stirred until all dissolved. 10.34 g calcium chloride dihydrate were dissolved in 200 mL water. The calcium chloride solution was heated to 40° C. and the pH was adjusted to 7.0. The alendronate-tripolyphosphonate solution was added into the calcium chloride solution dropwise, keeping the pH of the resulting solution at 7.0 by adding 1N NaOH. The precipitate was collected by filtration and washed with water. The solid was dried in an oven at 120° C. overnight. 8.82 g of calcium complex salt of alendronate with tripolyphosphate was thus obtained.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customThe solid was dried in an oven at 120° C. overnight

Sources & evidence

ORD record
ord-524d0fc7659e4a88a3c370b640756461
Source dataset
uspto-grants-2015_03
Patent number
US08974801B2

Reaction notes

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