HCID 15840468, compound → HCID 15840469, compound

HRID 341783Notes

Reaction equation

HRID 341783 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27]Br)=[CH:21][N:20]=1)[P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:29]([O-:32])(=[S:31])[CH3:30].[Na+]>CC(C)=O>[CH2:1]([O:3][P:4]([CH:9]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][S:31][C:29](=[O:32])[CH3:30])=[CH:21][N:20]=1)[P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 15840468HCID 15840468, compoundHCID 23700354HCID 23700354, compound

Product 1

HCID 15840469HCID 15840469, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of [(5-(3-bromopropyl)-2-pyridinyl)aminomethylene]bis[phosphonic acid] tetraethyl ester (5.0 mmol) is stirred in dry acetone (35 ml) and sodium thioacetate (5.2 mmol) is added. The mixture is stirred at 50° C. for 12 hours. After cooling to room temperature the solvent is removed under reduced pressure. The crude residue is dissolved in methylene chloride and washed with water. The organic layer is then dried and concentrated under reduced pressure. The desired product is purified by flash chromatography using a 5-10% isopropanol in methylene chloride gradient on silica gel.

Workup

  1. temperatureAfter cooling to room temperature the solvent
  2. customis removed under reduced pressure
  3. dissolutionThe crude residue is dissolved in methylene chloride
  4. washwashed with water
  5. customThe organic layer is then dried
  6. concentrationconcentrated under reduced pressure
  7. customThe desired product is purified by flash chromatography

Sources & evidence

ORD record
ord-a1bccd775bb549ed8836d06341f9eda4
Source dataset
uspto-grants-1999_01
Patent number
US05856314

Reaction notes

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