Sodium Hydroxide → Alendronate sodium anhydrous

HRID 1062840Notes

Reaction equation

HRID 1062840 reaction equation
[CH2:1]([CH2:13][NH2:14])[CH2:2][C:3]([P:9]([OH:12])([OH:11])=[O:10])([P:5]([OH:8])([OH:7])=[O:6])[OH:4].O.[OH-].[Na+:17]>C(O)C>[CH2:1]([CH2:13][NH2:14])[CH2:2][C:3]([P:5]([O-:7])([OH:8])=[O:6])([P:9]([OH:12])([OH:11])=[O:10])[OH:4].[Na+:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15585620Alendronic acid monohydrate2×

Product 1

HCID 16760285Alendronate sodium anhydrous

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A one liter flask was fitted with a mechanical stirrer, a thermometer, and a reflux condenser. The flask was charged with alendronic acid monohydrate (25 g, 0.094 mol) and aqueous ethanol. The mixture was heated to boiling with stirring. The aqueous ethanolic sodium hydroxide was added dropwise to the suspension of alendronic acid monohydrate in aqueous ethanol for 3 hours at reflux with vigorously stirring. Then the mixture was stirred at reflux for additional 15 hours. The mixture was cooled to room temperature with stirring. The solid was filtered, washed with absolute ethanol, then with absolute ethyl, and dried overnight in a vacuum oven (10-15 mm Hg, ambient temperature) to give 26.2 g of alendronate sodium, having crystalline Form G.

Workup

  1. customA one liter flask was fitted with a mechanical stirrer
  2. temperatureThe mixture was heated
  3. temperatureat reflux
  4. stirringwith vigorously stirring
  5. stirringThen the mixture was stirred
  6. temperatureat reflux for additional 15 hours
  7. stirringwith stirring
  8. filtrationThe solid was filtered
  9. washwashed with absolute ethanol
  10. customwith absolute ethyl, and dried overnight in a vacuum oven (10-15 mm Hg, ambient temperature)

Sources & evidence

ORD record
ord-2f79b029d907427c99ab0eaee26c242b
Source dataset
uspto-grants-2005_11
Patent number
US06963008B2

Reaction notes

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