Acetone → Ibandronate Sodium Anhydrous

HRID 229909Notes

Reaction equation

HRID 229909 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>O>[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 104%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
3 °C

Procedure

A solution of amorphous ibandronic acid (4.5 g) in water (9 ml) and sodium hydroxide (0.63 g, solid) was stirred at reflux temperature. The solution was poured into a cold acetone (100 ml). The resulting precipitate was stirred at 3° C. for 2 hours. The precipitate was isolated by vacuum filtration, washed with cold acetone (2×15 ml), and dried in a vacuum oven at 50° C. for 24 hours to obtain 5.0 g of ibandronate sodium crystal form Q4. Form Q4 can exhibit a weight loss of about 7% to about 8% in TGA.

Workup

  1. temperatureat reflux temperature
  2. customThe precipitate was isolated by vacuum filtration
  3. washwashed with cold acetone (2×15 ml)
  4. customdried in a vacuum oven at 50° C. for 24 hours

Sources & evidence

ORD record
ord-33472374d9974911bf1da30e8b88f18b
Source dataset
uspto-grants-2009_07
Patent number
US07563918B2

Reaction notes

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