Triethylamine → Ethyl 3-[3-([2-(diethoxyphosphoryl)propanoyl]aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionate

HRID 1816595

Reaction equation

HRID 1816595 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([CH3:13])[C:10]([OH:12])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[NH2:14][CH2:15][C:16]1[CH:17]=[C:18]([CH2:24][CH:25]([O:31][CH:32]([CH3:34])[CH3:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH2:7]([O:6][P:4]([CH:9]([CH3:13])[C:10]([NH:14][CH2:15][C:16]1[CH:17]=[C:18]([CH2:24][CH:25]([O:31][CH:32]([CH3:33])[CH3:34])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])=[O:12])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 118059462-diethylphosphonopropionic acidHCID 22493983Ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate

Product 1

HCID 22494119Ethyl 3-[3-([2-(diethoxyphosphoryl)propanoyl]aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionateYield 87.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

643 mg of 2-diethylphosphonopropionic acid and 973 mg of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionate were dissolved in 10 ml N,N-dimethylformamide, and 470 μl diethyl cyanophosphonate and 1.07 ml triethylamine were successively added thereto. The mixture was stirred overnight at room temperature, and the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 1.310 g of ethyl 3-[3-([2-(diethoxyphosphoryl)propanoyl]aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionate.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-008f4e5077ed4761a53b45479caa79fa
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Linked notes

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