Alendronic Acid → HCID 23051096, compound

HRID 1651030Notes

Reaction equation

HRID 1651030 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:14])([P:10]([OH:13])(=[O:12])[OH:11])[P:6]([OH:9])(=[O:8])[OH:7].[OH-].[Na+].[CH:17](=O)[CH2:18][CH:19]([CH3:21])[CH3:20]>[Pd]>[OH:14][C:5]([P:6]([OH:9])(=[O:7])[OH:8])([P:10]([OH:13])(=[O:11])[OH:12])[CH2:4][CH2:3][CH2:2][NH:1][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 2088Alendronic AcidHCID 115523-MethylbutanalHCID 14798Sodium Hydroxide

Product 1

HCID 23051096HCID 23051096, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4 g. 4-Amino-1-hydroxybutane-1,1-diphosphonic acid are dissolved in 64 ml. 1N aqueous sodium hydroxide solution, mixed with 3.8 ml. isovaleraldehyde and, after the addition of 2.5 g. of 10% palladium-charcoal, hydrogenated at a pressure of 5 bar. The course of the reaction is monitored electrophoretically until the starting material has disappeared. The reaction mixture is filtered, acidified with Amberlite R 120 (H+ form) and evaporated until crystallisation commences, 1.3 g. of crystals thus being obtained in a yield of 20% of theory; m.p. 225°-227° C. (decomp.); Mrel =0.39. 1-Hydroxy-4-(N-3-methylbutylamino)-butane-1,1-diphosphonic acid remaining in the mother liquor, which is formed as an intermediate, can be used again for the reductive alkylation.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated until crystallisation commences, 1.3 g
  3. customof crystals thus being obtained in a yield of 20% of theory

Sources & evidence

ORD record
ord-2d0c682dfb8e4ec7bff0cb179709f9fc
Source dataset
uspto-grants-1990_05
Patent number
US04927814

Reaction notes

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