Glycine methyl ester hydrochloride → HCID 19801611, compound

HRID 1646173Notes

Reaction equation

HRID 1646173 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16]Br)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Cl.[CH3:19][O:20][C:21](=[O:24])[CH2:22][NH2:23]>CO.C(N(CC)CC)C>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][NH:23][CH2:22][C:21]([O:20][CH3:19])=[O:24])([O:5][CH2:6][CH3:7])=[O:8])[CH3:2]

Participants

5

Reactant 2

HCID 122755Glycine methyl ester hydrochlorideHCID 151719952-(Diethylphosphonomethyl)benzyl bromide

Product 1

HCID 19801611HCID 19801611, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of the diethyl[[2(bromomethyl)phenyl]methyl]phosphonate (Example A) (0.9 g, 2.8 mmol) in methanol (25 ml) and triethylamine (5 ml) is treated with glycine methyl ester hydrochloride (0.71 g, 5.6 mmol) and heated at reflux in an oil bath for 19 hours. The solvent is removed in vacuo and the residue dissolved in water and extracted with chloroform. The chloroform layer is dried over magnesium sulfate, filtered, and evaporated. The oily residue is purified via silica gel chromatography (2-4% methanol in chloroform as eluant).

Workup

  1. temperatureheated
  2. temperatureat reflux in an oil bath for 19 hours
  3. customThe solvent is removed in vacuo
  4. dissolutionthe residue dissolved in water
  5. extractionextracted with chloroform
  6. dry with materialThe chloroform layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe oily residue is purified via silica gel chromatography (2-4% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-3c3a607969fc4b34b0b7fac8a867652d
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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