Acetone → Ibandronate Sodium Anhydrous

HRID 229929Notes

Reaction equation

HRID 229929 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:8][CH2:9][C:10]([P:16]([OH:19])([OH:18])=[O:17])([P:12]([OH:15])([OH:14])=[O:13])[OH:11])[CH3:7].[OH-].[Na+:21].CC(C)=O>C(#N)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:8][CH2:9][C:10]([P:16]([O-:19])([OH:18])=[O:17])([P:12]([OH:15])([OH:14])=[O:13])[OH:11])[CH3:7].[Na+:21]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 60852Ibandronate

Product 1

HCID 23670359Ibandronate Sodium AnhydrousYield 65.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A slurry of amorphous ibandronic acid (5 g) in acetonitrile (200 ml) was stirred at reflux temperature. Solid sodium hydroxide (0.63 g) was added, and the reaction mixture was stirred at reflux temperature for an additional 2 hours. Acetone (50 ml) was added dropwise. Then the reaction mixture was cooled to room temperature and stirred for 16 hours. The precipitate was isolated by vacuum filtration, washed with acetone (50 ml), and dried in a vacuum oven at 50° C. for 22 hours to obtain 3.5 g of amorphous ibandronate sodium.

Workup

  1. temperatureat reflux temperature
  2. temperatureat reflux temperature for an additional 2 hours
  3. stirringstirred for 16 hours
  4. customThe precipitate was isolated by vacuum filtration
  5. washwashed with acetone (50 ml)
  6. customdried in a vacuum oven at 50° C. for 22 hours

Sources & evidence

ORD record
ord-51130f10f9a5441d94d9847a07123d87
Source dataset
uspto-grants-2009_07
Patent number
US07563918B2

Reaction notes

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