Alendronic Acid → HCID 131719112, compound

HRID 1757613Notes

Reaction equation

HRID 1757613 reaction equation
C([O:4][CH2:5][C:6](Cl)=[O:7])(=O)C.[NH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:22])([P:18]([OH:21])(=[O:20])[OH:19])[P:14]([OH:17])(=[O:16])[OH:15].[OH-].[Na+:24]>O.CN(C=O)C>[Na+:24].[Na+:24].[Na+:24].[OH:4][CH2:5][C:6]([NH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:22])([P:14]([O-:17])(=[O:15])[OH:16])[P:18]([O-:21])(=[O:19])[O-:20])=[O:7]

Participants

6

Reactant 3

HCID 2088Alendronic AcidHCID 14798Sodium Hydroxide2×HCID 26297Acetoxyacetyl chloride

Product 1

HCID 131719112HCID 131719112, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Acetoxyacetyl chloride (0.324 ml) is dropped into a solution of 4-amino-1-hydroxybutane-1,1-diphosphonic acid (500 mg) in water (5 ml) and1N NaOH (8 ml), simultaneously adding 1N NaOH (3 ml) to maintain pH between11 and 12. When the additions are completed, the reaction mixture is stirred at room temperature for 2 hours, then it is diluted with DMF: a precipitate separates which is recovered by centrifugation and purified byredissolution in water (3 ml) and reprecipitated with acetone (30 ml), to give 720 mg of N-(hydroxyacetyl)-4-amino-1-hydroxybutane-1,1-diphosphonic acid trisodium salt; m.p. >260°

Workup

  1. temperatureto maintain pH between11 and 12
  2. customa precipitate separates which is recovered by centrifugation
  3. custompurified byredissolution in water (3 ml)
  4. customreprecipitated with acetone (30 ml)

Sources & evidence

ORD record
ord-96007d2ea82e414ba6d789bc634fdcf9
Source dataset
uspto-grants-1995_08
Patent number
US05446187

Reaction notes

Loading…