Hydrochloric Acid → HCID 10276319, compound

HRID 1794460Notes

Reaction equation

HRID 1794460 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]1[CH:23]=[CH:22][C:21]([C:24]2[O:28][N:27]=[CH:26][C:25]=2[CH2:29][CH2:30][C:31](O)=[O:32])=[CH:20][CH:19]=1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[CH2:12]([O:11][P:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:31](=[O:32])[CH2:30][CH2:29][C:25]2[CH:26]=[N:27][O:28][C:24]=2[C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)=[CH:16][CH:15]=1)([O:8][CH2:9][CH3:10])=[O:14])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 88358Diethyl p-aminobenzylphosphonateHCID 181649HOAtHCID 22221136HCID 22221136, compound

Product 1

HCID 10276319HCID 10276319, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of diethyl 4-aminobenzylphosphonate (0.73 g), 3-[5-(4-fluorophenyl)-4-isoxazolyl]propionic acid (0.49 g), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (HOAT) (0.40 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSCI) (0.45 g) and N,N-dimethylformamide (5 ml) was stirred at room temperature overnight. The reaction mixture was poured into a 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The ethyl acetate layer was washed with 10% aqueous potassium carbonate solution, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from ethyl acetate-hexane to give N-[4-(diethylphosphonomethyl)phenyl]-3-[5-(4-fluorophenyl)-4-isoxazolyl]propionamide (0.67 g, yield 70%) as a colorless prism. melting point: 134–135° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 10% aqueous potassium carbonate solution
  3. dry with materialwith saturated brine, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe obtained solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8059e519bade42d9a9e0928f9db91ef4
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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