Sodium Hydroxide → HCID 23670154, compound

HRID 1612766Notes

Reaction equation

HRID 1612766 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)([OH:15])[CH2:5][P:6]([CH2:11][CH2:12][CH2:13][CH3:14])(=[O:10])[O:7]CC.[OH-].[Na+:24]>C(O)C.O>[NH2:2][CH2:3][C:4]([C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)([OH:15])[CH2:5][P:6]([CH2:11][CH2:12][CH2:13][CH3:14])(=[O:7])[O-:10].[Na+:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19776491HCID 19776491, compound

Product 1

HCID 23670154HCID 23670154, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.2 g of ethyl 3-amino-2-(4-chlorophenyl)-2-hydroxy-propyl(n-butyl)phosphinate hydrochloride in 5 ml of ethanol is treated with 0.24 g of sodium hydroxide dissolved in 3 ml of water. The solution heated to 60° for 20 hours. After this time the solution is cooled to room temperature and washed 2-times with 50 ml each of dichloromethane and once with 50 ml of diethyl ether. The aqueous phase is evaporated to dryness. The residue is suspended in n-propanol, heated to 80° C. for 10 minutes and filtered. The n-propanol is removed in vacuo to afford a white solid. Chromatography on reverse-phase silica gel followed by drying in vacuo at 80° yields sodium 3-amino-2-(4-chlorophenyl)-2-hydroxy-propyl(n-butyl)phosphinate; m.p. 215°-215.5°; 1H-NMR spectrum (D2O): δ=7.4 ppm (4H, s), 2.91 ppm (2H, ABq), 2.22 ppm (2H, ABq,d), 1.37-1.0 ppm (6 H, m), 0.75 ppm (3H, t).

Workup

  1. temperatureThe solution heated to 60° for 20 hours
  2. washwashed 2-times with 50 ml each of dichloromethane and once with 50 ml of diethyl ether
  3. customThe aqueous phase is evaporated to dryness
  4. temperatureheated to 80° C. for 10 minutes
  5. filtrationfiltered
  6. customThe n-propanol is removed in vacuo
  7. customto afford a white solid
  8. customby drying in vacuo at 80°

Sources & evidence

ORD record
ord-eebd343b2f6545c98ace5e377cbc80c5
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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