Hydrochloric Acid → (3-Amino-1-methyl-propyl)-methyl-phosphinic acid

HRID 2210763Notes

Reaction equation

HRID 2210763 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH:5]([P:7]([CH3:14])(=[O:13])[O:8]CC(C)C)[CH3:6]>>[NH2:2][CH2:3][CH2:4][CH:5]([P:7]([CH3:14])(=[O:8])[OH:13])[CH3:6]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23374771isobutyl P-(4-aminobut-2-yl)-P-methyl-phosphinate

Product 1

HCID 10219532(3-Amino-1-methyl-propyl)-methyl-phosphinic acid

Procedure

A solution of 21.5 g of isobutyl P-(4-aminobut-2-yl)-P-methyl-phosphinate 80 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 10 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated twice with 100 ml of water. The crude material is dissolved in water, washed with chloroform, and the aqueous layer treated with activated charcoal. The aqueous solution is filtered hot, evaporated to dryness, the crude product is dissolved in 50 ml of methanol and treated with 1-2 ml of propylene oxide. The hygroscopic solid is filtered and triturated with acetone. After drying, P-(4-aminobut-2-yl)-P-methyl-phosphinic acid is obtained as a hygroscopic solid, m.p. 68°-75°, 31P-NMR spectrum: δ=+46.5 ppm (D2O).

Workup

  1. temperatureto reflux for a period of 10 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude material is dissolved in water
  4. washwashed with chloroform
  5. additionthe aqueous layer treated with activated charcoal
  6. filtrationThe aqueous solution is filtered hot
  7. customevaporated to dryness
  8. dissolutionthe crude product is dissolved in 50 ml of methanol
  9. additiontreated with 1-2 ml of propylene oxide
  10. filtrationThe hygroscopic solid is filtered
  11. customtriturated with acetone
  12. customAfter drying

Sources & evidence

ORD record
ord-3f58d52094ef4b53a48c46d77406a435
Source dataset
uspto-grants-1995_10
Patent number
US05461040

Reaction notes

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