p-Aminophenylacetic acid ethyl ester → HCID 69562013, compound

HRID 1794451Notes

Reaction equation

HRID 1794451 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][C:15]1[C:19](/[CH:20]=[CH:21]/[C:22](O)=[O:23])=[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:17][N:16]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O.CN(C)C=O>[CH2:12]([O:11][C:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:22](=[O:23])/[CH:21]=[CH:20]/[C:19]2[C:15]([CH3:14])=[N:16][O:17][C:18]=2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:7][CH:6]=1)=[O:10])[CH3:13]

Participants

7

Reactant 4

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69561163HCID 69561163, compound

Product 1

HCID 69562013HCID 69562013, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-aminophenylacetate (1.11 g), (E)-3-(3-methyl-5-phenyl-4-isoxazolyl)propenoic acid (0.95 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (0.75 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.91 g) and N,N-dimethylformamide (20 ml) was stirred at room temperature overnight. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and (E)-N-(4-ethoxycarbonylmethylphenyl)-3-(3-methyl-5-phenyl-4-isoxazolyl)propenamide (1.82 g, yield 97%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 164–165° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with dilute hydrochloric acid, saturated aqueous sodium hydrogencarbonate
  3. dry with materialsaturated brine, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b7c0d5135af5425fbc0209fa3bff4c3f
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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