HCID 23700354, compound → HCID 86752763, compound

HRID 963644Notes

Reaction equation

HRID 963644 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH2:7][NH:8][C:9]2[C:13]([CH:14]=1)=[CH:12][C:11]([P:23]([O:28][CH2:29][CH3:30])(=[O:27])[O:24][CH2:25][CH3:26])([P:15]([O:20][CH2:21][CH3:22])(=[O:19])[O:16][CH2:17][CH3:18])[CH:10]=2.[C:31]([O-:34])(=[S:33])[CH3:32].[Na+]>CC(C)=O>[C:31]([S:33][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH2:7][NH:8][C:9]2[C:13]([CH:14]=1)=[CH:12][C:11]([P:23]([O:28][CH2:29][CH3:30])(=[O:27])[O:24][CH2:25][CH3:26])([P:15]([O:20][CH2:21][CH3:22])(=[O:19])[O:16][CH2:17][CH3:18])[CH:10]=2)(=[O:34])[CH3:32]

Participants

4

Reactant 2

HCID 23700354HCID 23700354, compoundHCID 86752764HCID 86752764, compound

Product 1

HCID 86752763HCID 86752763, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of dihydro-3-(4-bromobutyl)-1-pyrindine-6,6-bisphosphonic 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-f40eaf98417b43ebab1bdd10e8c41790
Source dataset
uspto-grants-1998_06
Patent number
US05763611

Reaction notes

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