Ethyl bromoacetate → HCID 90013734, compound

HRID 1499013Notes

Reaction equation

HRID 1499013 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(#N)C>[CH2:12]([O:11][P:7]([CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([O:8][CH2:9][CH3:10])=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 54204764HCID 54204764, compound

Product 1

HCID 90013734HCID 90013734, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

The mixture of diethyl 2-(2-hydroxyethylamino)ethylphosphonate (6 g, 26.7 mmol) and K2CO3 (3.7 g, 26.7 mmol) in dry acetonitrile (80 ml) was cooled to −10° C. and ethyl bromoacetate (6.7 g, 40 mmol) was added. The reaction mixture was stirred at −10° C. for 1 h and then at room temperature for 2 days. The solvent was then removed by evaporation. Water and CHCl3 were added, the organic layer separated, washed with brine and dried over anhydrous MgSO4. After filtration, solvent was evaporated and the residue was purified by column chromatography on silica gel (CHCl3-MeOH), the ethyl 2-((2-(diethoxyphosphoryl)ethyl)(2-hydroxyethyl)amino)acetate was obtained in 64% yield (5.32g).

Workup

  1. waitat room temperature for 2 days
  2. customThe solvent was then removed by evaporation
  3. additionWater and CHCl3 were added
  4. customthe organic layer separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationAfter filtration, solvent
  8. customwas evaporated
  9. customthe residue was purified by column chromatography on silica gel (CHCl3-MeOH)

Sources & evidence

ORD record
ord-0c5592412e7d40b598c7eafae7493749
Source dataset
uspto-grants-2015_12
Patent number
US09200020B2

Reaction notes

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