Potassium Hydroxide → HCID 19801619, compound

HRID 1646180Notes

Reaction equation

HRID 1646180 reaction equation
C([O:3][P:4]([O:21]CC)([CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:5])C.[OH-].[K+]>C(OCC)C.O>[P:4](/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]([OH:18])=[O:17])([OH:21])([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54340865HCID 54340865, compound

Product 1

HCID 19801619HCID 19801619, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl N-[2-[2-(diethoxyphosphinyl)ethenyl]phenyl]glycinate (Example 2b)(1.3 g, 3.8 mmol) in diethyl ether (15 ml) is treated with potassium trimethylsilanoate (0.54 g, 4.2 mmol) and stirred over the weekend. The diethyl ether is removed and the oily residue suspended in acetonitrile (50 ml) and stirred under a nitrogen atmosphere for 30 minutes and further treated with trimethylsilylbromide (3 ml) and stirred at room temperature for four hours. 1H-NMR indicates some ester remains so the acetonitrile is removed and the residue is treated with a solution of potassium hydroxide (0.56 g, 10 mmol) in water (3 ml) and stirred for 16 hours. The water is removed and the residue purified on Dowex 50×400 ion exchange resin (water and 2N ammonium hydroxide as eluants). The desired material (fluorescent on tlc under uv light, ninhydrin positive) is obtained from the water eluate as a light, green-white solid (0.12 g).

Workup

  1. customThe diethyl ether is removed
  2. stirringstirred under a nitrogen atmosphere for 30 minutes
  3. additionfurther treated with trimethylsilylbromide (3 ml)
  4. stirringstirred at room temperature for four hours
  5. customis removed
  6. stirringstirred for 16 hours
  7. customThe water is removed
  8. customthe residue purified on Dowex 50×400 ion exchange resin (water and 2N ammonium hydroxide as eluants)

Sources & evidence

ORD record
ord-b6eb8c18606e4da3a8e05708ca9a7cca
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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