Hydrochloric Acid → HCID 86591387, compound

HRID 1794464Notes

Reaction equation

HRID 1794464 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.[Cl:17][C:18]1[CH:19]=[C:20]([C:25]2[O:29][N:28]=[CH:27][C:26]=2[CH2:30][CH2:31][C:32](O)=[O:33])[CH:21]=[CH:22][C:23]=1[F:24].ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([C:25]2[O:29][N:28]=[CH:27][C:26]=2[CH2:30][CH2:31][C:32]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][P:7]([O:8][CH2:9][CH3:10])([O:11][CH2:12][CH3:13])=[O:14])=[CH:15][CH:16]=2)=[O:33])[CH:21]=[CH:22][C:23]=1[F:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 88358Diethyl p-aminobenzylphosphonateHCID 181649HOAtHCID 22221113HCID 22221113, compound

Product 1

HCID 86591387HCID 86591387, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of diethyl 4-aminobenzylphosphonate (36 mg), 3-[5-(3-chloro-4-fluorophenyl)-4-isoxazolyl]propionic acid (27 g), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (20 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (30 mg) and N,N-dimethylformamide (0.5 ml) was stirred at room temperature overnight. The reaction mixture was poured into 1N aqueous hydrochloric acid solution and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated, and the obtained solid was purified by preparative HPLC to give 3-[5-(3-chloro-4-fluorophenyl)-4-isoxazolyl]-N-[4-(diethylphosphonomethyl)phenyl]propionamide.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. customthe obtained solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-509ededeed6044618e792ff0a7c0c8d8
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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