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

HRID 1816594Notes

Reaction equation

HRID 1816594 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([OH:12])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[NH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH2:23][CH:24]([O:30][CH:31]([CH3:33])[CH3:32])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22].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]([CH2:9][C:10]([NH:13][CH2:14][C:15]1[CH:16]=[C:17]([CH2:23][CH:24]([O:30][CH:31]([CH3:32])[CH3:33])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22])=[O:12])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 36704(Diethoxyphosphinyl)acetic acidHCID 76257Diethyl cyanophosphonateHCID 22493983Ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate

Product 1

HCID 22494247Ethyl 3-[3-([2-(diethoxyphosphoryl)acetyl]aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionateYield 95.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

600 mg diethylphosphonoacetic acid and 969 mg of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionate were dissolved in 10 ml N,N-dimethylformamide, followed by the successive addition of 470 μl diethyl cyanophosphonate and 1.07 ml triethylamine. 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. Thus, 1.387 g of ethyl 3-[3-([2-(diethoxyphosphoryl)acetyl]aminomethyl)-4-methoxyphenyl]-2-isopropoxypropionate was obtained.

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-857dc13a30a741e983148dc445924cf1
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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