Potassium Carbonate → HCID 19801592, compound

HRID 1646181Notes

Reaction equation

HRID 1646181 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:8][O:9][C:10](=[O:13])[CH2:11][NH2:12].Br[CH2:15][CH2:16][S:17][CH2:18][P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22]>CN(C)C=O>[CH2:21]([O:20][P:19]([CH2:18][S:17][CH2:16][CH2:15][NH:12][CH2:11][C:10]([O:9][CH3:8])=[O:13])([O:23][CH2:24][CH3:25])=[O:26])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122755Glycine methyl ester hydrochlorideHCID 54360717HCID 54360717, compound

Product 1

HCID 19801592HCID 19801592, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of potassium carbonate (0.42 g, 3 mmol) in anhydrous dimethylformamide (3 ml) is treated with glycine methyl ester hydrochloride (0.25 g, 2 mmol) and stirred under nitrogen. After 5 minutes diethyl (2-bromoethyl)thiomethylphosphonate (Example G) (0.28 g, 1.08 mmol) is added as a solution in dimethylformamide (0.5 ml). After stirring 48 hours, the dimethylformamide is removed in vacuo, and the residue is dissolved in water and extracted with chloroform (2×30 ml). The organic layer is separated, dried over sodium sulfate, filtered, evaporated, and the residue is purified by silica gel chromatography (60:1 chloroform:methanol as eluant) to give methyl N-[2-[[(diethoxyphosphinyl)methyl]thio]ethyl]glycinate.

Workup

  1. stirringAfter stirring 48 hours
  2. customthe dimethylformamide is removed in vacuo
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with chloroform (2×30 ml)
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue is purified by silica gel chromatography (60:1 chloroform:methanol as eluant)

Sources & evidence

ORD record
ord-c8b1dce742324c1291bfc9ddf57bfa5e
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

Loading…