1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[4-(diethylphosphonomethyl)phenyl]-3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionamide

HRID 1794461Notes

Reaction equation

HRID 1794461 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[F:17][C:18]([F:36])([F:35])[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][N:28]=[CH:27][C:26]=2[CH2:30][CH2:31][C:32](O)=[O:33])=[CH:21][CH:20]=1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O>[CH2:12]([O:11][P:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:32](=[O:33])[CH2:31][CH2:30][C:26]2[CH:27]=[N:28][O:29][C:25]=2[C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:35])([F:17])[F:36])=[CH:20][CH:21]=2)=[CH:16][CH:15]=1)([O:8][CH2:9][CH3:10])=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 88358Diethyl p-aminobenzylphosphonateHCID 181649HOAtHCID 222214183-[5-(4-Trifluoromethylphenyl)-4-isoxazolyl]propionic acid

Product 1

HCID 86591384N-[4-(diethylphosphonomethyl)phenyl]-3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionamideYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of diethyl 4-aminobenzylphosphonate (72.9 mg), 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionic acid (57 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (40 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (45 mg) and N,N-dimethylformamide (0.3 ml) was stirred at room temperature overnight. The reaction mixture was directly introduced into preparative HPLC and purified to give N-[4-(diethylphosphonomethyl)phenyl]-3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionamide.

Workup

  1. additionThe reaction mixture was directly introduced into preparative HPLC
  2. custompurified

Sources & evidence

ORD record
ord-c6fd746efaa64864be40a627f6b4417f
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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