Acetic Acid → HCID 19090878, compound

HRID 973591Notes

Reaction equation

HRID 973591 reaction equation
[OH:1][CH:2]([CH2:16][N:17]1C(=O)C2=CC=CC=C2C1=O)[CH2:3][PH:4]([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([O-:8])[O:5][CH2:6][CH3:7].O.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C>[NH2:17][CH2:16][CH:2]([OH:1])[CH2:3][P:4]([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])(=[O:8])[O:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 178472282HCID 178472282, compound

Product 1

HCID 19090878HCID 19090878, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1.0 g of ethyl 2-hydroxy-3-phthalimido-propyl(diethoxymethyl)phosphonite in 23 ml of isopropanol is added 4 ml of water. To this mixture is added 0.47 g of sodium borohydride and this is stirred for a period of 24 hours at room temperature. After this time 2.6 ml of glacial acetic acid are carefully added and the reaction heated to 80° for a period of 2 hours. After this time, the reaction is cooled to room temperature, the solvent evaporated under reduced pressure and the residue passed down a silica column using a mixture of one part ethyl acetate to one part ethanol as eluant. Ethyl 3-amino-2-hydroxy-propyl(diethoxymethyl)phosphinate is obtained as colourless oil, 31P=+45.8 and +45.2 ppm (CDCl3).

Workup

  1. temperaturethe reaction heated to 80° for a period of 2 hours
  2. temperatureAfter this time, the reaction is cooled to room temperature
  3. customthe solvent evaporated under reduced pressure
  4. additiona mixture of one part ethyl acetate to one part ethanol as eluant

Sources & evidence

ORD record
ord-00143520b7eb4c35b036ccf92f215a14
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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