4-Phenoxybenzoic acid → HCID 67146952, compound

HRID 2422200Notes

Reaction equation

HRID 2422200 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[O:15]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[O:15]([C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)=[O:27])=[CH:29][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 751824-Phenoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10442595Ethyl 3-(4-aminophenyl)propanoate

Product 1

HCID 67146952HCID 67146952, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-aminobenzenepropanoate (0.70 g, 3.6 mmol) in N,N-dimethylformamide (25 mL) were added 4-phenoxybenzoic acid (0.85 g, 4.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.76 g, 4.0 mmol) and 1-hydroxybenzotriazole monohydrate (0.61 g, 4.0 mmol), and the mixture was stirred at room temperature for 16 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2:1) to give the title compound (0.96 g, yield 68%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-eba030d9d1a34dec88dc02e131356ab5
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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