Sodium Hydroxide → Alendronate sodium anhydrous

HRID 2122078Notes

Reaction equation

HRID 2122078 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 250 ml flask was fitted with a mechanical stirrer, a thermometer, a dropping funnel, and a reflux condenser. The flask was charged with alendronic acid monohydrate (5 g, 0.019 mol) and aqueous ethanol. The aqueous ethanolic sodium hydroxide was added dropwise to the suspension of alendronic acid monohydrate in aqueous ethanol for 15 minutes at reflux with vigorously stirring. The mixture was then refluxed for additional 15 hours. The mixture was then cooled to room temperature with stirring. The solid was filtered, washed with absolute ethanol, then with absolute ethyl ether, and dried overnight in a vacuum oven (10-15 mm Hg, ambient temperature) to give 5.2 g of alendronate sodium, having crystalline Form H.

Workup

  1. customA 250 ml flask was fitted with a mechanical stirrer
  2. temperatureat reflux
  3. temperatureThe mixture was then refluxed for additional 15 hours
  4. stirringwith stirring
  5. filtrationThe solid was filtered
  6. washwashed with absolute ethanol
  7. dry with materialwith absolute ethyl ether, and dried overnight in a vacuum oven (10-15 mm Hg, ambient temperature)

Sources & evidence

ORD record
ord-bec05a6d49944bd8a481b064559358e8
Source dataset
uspto-grants-2004_02
Patent number
US06696601B2

Reaction notes

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