Methanol → HCID 19801610, compound

HRID 1646177Notes

Reaction equation

HRID 1646177 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].CO>C1(C)C=CC=CC=1>[CH2:16]([O:15][P:11]([CH2:10][C:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:9]=[CH:8][CH:7]=1)([O:12][CH2:13][CH3:14])=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 15171984HCID 15171984, compound

Product 1

HCID 19801610HCID 19801610, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of diethyl [[3-(2-aminoethyl)phenyl]methyl]phosphonate (Example D) (3.6 g, 13.2 mmol) in toluene (15 ml) and triethylamine (2.7 g, 26.4 mmol) is cooled in an ice/salt bath and a solution of ethyl bromoacetate (2.2 g, 13.2 mmol) in toluene (8 ml) is added dropwise over 20 minutes. A gum forms and methanol (5 ml) is added and stirred an additional two hours. After evaporation of the solvent, the residue is dissolved in ethyl acetate (75 ml) and washed with water (20 ml, and 10 ml) and then saturated sodium chloride solution (10 ml). The organic layer is dried over magnesium sulfate, filtered, and evaporated to give an oil (4.3 g). Chromatography over silica gel gives an analytical, colorless oil. 1H-NMR: 4H, m, 7.33-7.0 ppm; 6H, m, 4.33-3.86; 2H, s, 3.40; 2H, d, 3.13; 4H, m, 2.90-2.70; 1H, s, 1.8; 9H, m, 1.33-1.10.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in ethyl acetate (75 ml)
  3. washwashed with water (20 ml, and 10 ml)
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6466d557f6364f3c9c5097af0aba93e5
Source dataset
uspto-grants-1993_01
Patent number
US05179085

Reaction notes

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