HCID 23700354, compound → HCID 54016127, compound

HRID 341787Notes

Reaction equation

HRID 341787 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([P:21](=[O:24])([OH:23])[OH:22])[CH:10]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:11][CH2:12][CH2:13]Br)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:25]([O-:28])(=[S:27])[CH3:26].[Na+]>CC(C)=O>[CH2:1]([O:3][P:4]([CH:9]([P:21](=[O:24])([OH:23])[OH:22])[CH:10]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:11][CH2:12][CH2:13][S:27][C:25](=[O:28])[CH3:26])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 23700354HCID 23700354, compoundHCID 54403050HCID 54403050, compound

Product 1

HCID 54016127HCID 54016127, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of [5-bromo-2-(3-pyridinyl)pentylidene]bis [phosphonic acid] diethyl 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-569592eae4964e1a84236c6db67d3590
Source dataset
uspto-grants-1999_01
Patent number
US05856314

Reaction notes

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