Hydrochloric Acid → N-(Carboxymethyl)-N-(phosphonomethyl)-beta-alanine

HRID 1906117Notes

Reaction equation

HRID 1906117 reaction equation
Cl.[P:2]([OH:5])([OH:4])[OH:3].[C:6]([CH2:9][CH2:10][NH:11][CH2:12][C:13]([OH:15])=[O:14])([OH:8])=[O:7].[CH2:16]=O>O>[C:6]([CH2:9][CH2:10][N:11]([CH2:16][P:2]([OH:5])([OH:4])=[O:3])[CH2:12][C:13]([OH:15])=[O:14])([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 107909Phosphorous acidHCID 281622N-(Carboxymethyl)-beta-alanine

Product 1

HCID 4360398N-(Carboxymethyl)-N-(phosphonomethyl)-beta-alanineYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a three neck round bottom flask equipped with an addition funnel, a reflux condenser, and a stir bar was added 50 mL of water, 50 mL of concentrated hydrochloric acid, and 10.7 g (0.13 mol) of phosphorous acid. The solution was stirred and heated at reflux and then treated with 18.3 g (0.10 mol) of N-(2-carboxyethyl)glycine. Then 9.8 mL of a 40% (w/v) formaldehyde solution was added dropwise over 30 minutes. Heating was continued an additional 60 minutes. The solvent was then removed under reduced pressure until only a few mL remained. This was allowed to sit at 5° C. during which time a precipitate formed. This solid was filtered, washed with ethanol, and dried. The solvent was removed from the filtrate under reduced pressure. The residue was chromatographed on Dowex 50X8-400 ion exchange resin using water as the eluent. Combined with the initial precipitate, the ma3or fraction gave a total of 12.7 g (52%) of N-(2-carboxyethyl)-N-phosphonomethylglycine.

Workup

  1. customIn a three neck round bottom flask equipped with an addition funnel, a reflux condenser, and a stir bar
  2. temperatureheated
  3. temperatureat reflux
  4. temperatureHeating
  5. customThe solvent was then removed under reduced pressure until only a few mL
  6. customto sit at 5° C. during which time
  7. customformed
  8. filtrationThis solid was filtered
  9. washwashed with ethanol
  10. customdried
  11. customThe solvent was removed from the filtrate under reduced pressure
  12. customThe residue was chromatographed on Dowex 50X8-400 ion exchange resin

Sources & evidence

ORD record
ord-777e482f56354a308c07746ef8a16e23
Source dataset
uspto-grants-1987_03
Patent number
US04650613

Reaction notes

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