3-Benzyloxycarbonylaminopropyl(dodecyl)phosphinic acid → 3-Aminopropyl(dodecyl)phosphinic acid

HRID 973608Notes

Reaction equation

HRID 973608 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][P:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:17])[OH:16])=O)C1C=CC=CC=1>Cl>[NH2:11][CH2:12][CH2:13][CH2:14][P:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:16])[OH:17]

Participants

3

Reactant 1

HCID 190908573-Benzyloxycarbonylaminopropyl(dodecyl)phosphinic acid

Product 1

HCID 99220843-Aminopropyl(dodecyl)phosphinic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2.4 g of 3-benzyloxycarbonylaminopropyl(dodecyl)phosphinic acid in 50 ml of 36% hydrochloric acid is refluxed for 3 hours. During this time, a white precipitate is formed. After cooling to room temperature the acid is removed by co-evaporation with 6×50 ml of water on a rotary evaporator. The crude product is then dissolved in 50 ml of ethanol and stirred with 5 ml of propylene oxide. Filtration and drying gives 3-aminopropyl(dodecyl)phosphinic acid as a white solid m.p. 175°-7°. 31P-NMR=43.0 ppm (NaOD).

Workup

  1. customDuring this time, a white precipitate is formed
  2. customis removed by co-evaporation with 6×50 ml of water on a rotary evaporator
  3. dissolutionThe crude product is then dissolved in 50 ml of ethanol
  4. filtrationFiltration
  5. customdrying

Sources & evidence

ORD record
ord-2ae5587b5fe54434836803b535f55f7b
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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