Benzyl chloroformate → HCID 178523374, compound

HRID 2050689Notes

Reaction equation

HRID 2050689 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][PH:5](=[O:7])[OH:6].[OH-].[Na+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>O>[CH2:14]([O:13][C:11]([NH:1][CH2:2][CH2:3][CH2:4][PH:5](=[O:6])[OH:7])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 1219563-Aminopropylphosphinic acid

Product 1

HCID 178523374HCID 178523374, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.0 g of 3-aminopropylphosphinic acid in 200 ml of water is cooled to 5° , and the pH adjusted to 9.5 with 2 molar sodium hydroxide solution. To this mixture is added 6.8 g of benzyl chloroformate whilst maintaining the pH and temperature. After the addition is complete the mixture is stirred for 3 hours at pH 9.5 at room temperature and left to stand overnight. The mixture is then extracted with 100 ml of ether and the aqueous layer stirred at 5° with an equal volume of chloroform. The mixture is acidified to pH 2, the chloroform layer separated, dried over magnesium sulfate and the solvent evaporated under reduced pressure. The oily product is triturated with ether to give a white solid, 3-(N-benzyloxycarbonylamino)propylphosphinic acid, m.p. 53-55°, 31P-NMR : δ=+36.6 ppm (CDCl3).

Workup

  1. temperaturewhilst maintaining the pH and temperature
  2. additionAfter the addition
  3. waitleft
  4. waitto stand overnight
  5. extractionThe mixture is then extracted with 100 ml of ether
  6. stirringthe aqueous layer stirred at 5° with an equal volume of chloroform
  7. customthe chloroform layer separated
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent evaporated under reduced pressure
  10. customThe oily product is triturated with ether

Sources & evidence

ORD record
ord-d0475a5cc9854f2a9f1908a34a9e55d3
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

Loading…