Phosphonic acid → 2-Amino-7-phosphonoheptanoic acid

HRID 1632684Notes

Reaction equation

HRID 1632684 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].[NH2:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10]N.CO.[CH2:17](OCC)C>O.N1C=CC=CC=1>[NH2:5][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:17][P:1]([OH:3])([OH:2])=[O:4])[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 407Phosphonic acidHCID 887MethanolHCID 3283Diethyl EtherHCID 5962L-Lysine

Product 1

HCID 31222-Amino-7-phosphonoheptanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Equimolar quantities of the phosphonic acid, and L-lysine, were dissolved in water and warmed for 1/2 hr at 60° C. Two volumes of hot methanol were then added and the mixture brought to room temperature. Diethyl ether was added carefully, until a slight cloudiness appeared in the solution, which was left to stand. The phosphonic acid/lysine salt was filtered off and dissolved in water. A "Dowex" 50×8 column was prepared by passed 2M pyridine down it, and washing with water, the lysine salt solution was passed down the column and washed through with water, the phosphonic acid passing straight through. The amine acid containing fractions were collected and evaporated to dryness; a solution of known concentration was then made up, and the rotation of plane polarised light recorded on a "TBL" Automatic Polarimeter 143D using a mercury lamp. The first isomer to be precipitated was found to be (-), and circular dichroism studies indicated it to have the D configuration.

Workup

  1. custombrought to room temperature
  2. waitwas left
  3. filtrationThe phosphonic acid/lysine salt was filtered off
  4. dissolutiondissolved in water
  5. customA "Dowex" 50×8 column was prepared
  6. washwashing with water
  7. washwashed through with water
  8. additionThe amine acid containing fractions
  9. customwere collected
  10. customevaporated to dryness
  11. concentrationa solution of known concentration
  12. customThe first isomer to be precipitated

Sources & evidence

ORD record
ord-0958912bfead46b98b2c037187f55ff2
Source dataset
uspto-grants-1984_10
Patent number
US04477391

Reaction notes

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