Sodium Hydroxide → HCID 131719994, compound

HRID 54913Notes

Reaction equation

HRID 54913 reaction equation
[CH2:1]([NH:16][CH:17]([P:26](=[O:33])([O:30]CC)[O:27]CC)[P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])/[CH:2]=[C:3](/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])\[CH3:4].[OH-].[Na+:35]>C(O)C>[Na+:35].[Na+:35].[CH2:20]([O:19][P:18]([CH:17]([NH:16][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])\[CH3:4])[P:26](=[O:27])([O-:30])[O-:33])(=[O:25])[O:22][CH2:23][CH3:24])[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131719995HCID 131719995, compound

Product 1

HCID 131719994HCID 131719994, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of tetraethyl (E,E)-farnesylaminomethylenebisphosphonate (2.42 g) in ethanol (25 ml) was added to a solution of sodium hydroxide (0.40 g) in ethanol (25 ml). The mixture was stirred under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (5.0 ml). The solution was subjected to ion-exchange chromatography [Amberlite CG-50 (H+ -type)] to obtain (E,E)-farnesylaminomethylenebisphosphonic acid diethyl ester disodium salt (0.75 g, 29%). Colorless powder, mp: 116°-118° C. Elemental Analysis for C20H37NO6P2Na2.5/2H2O: Calcd.: C, 44.45; H, 7.83; N, 2.59 Found: C, 44.08; H, 7.60; N, 2.59

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in water (5.0 ml)

Sources & evidence

ORD record
ord-fdccd8bfd6fb40e0ae64c2c4500e6029
Source dataset
uspto-grants-1997_04
Patent number
US05624917

Reaction notes

Loading…