Benzyl chloroformate → HCID 178523374, compound

HRID 1612669Notes

Reaction equation

HRID 1612669 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-1262cd8b72c94c4090b7f57ff6ce8743
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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