Homovanillic Acid → 4-Hydroxy-3-methoxyphenylacetic acid pentafluorophenyl ester

HRID 7054

Reaction equation

HRID 7054 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][CH3:13].[F:14][C:15]1[C:20](O)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[F:14][C:15]1[C:20]([O:10][C:9](=[O:11])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:12][CH3:13])[CH:4]=2)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25]

Participants

5

Reactant 3

HCID 1738Homovanillic AcidHCID 13041PentafluorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 225073804-Hydroxy-3-methoxyphenylacetic acid pentafluorophenyl esterYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-hydroxy-3-methoxyphenylacetic acid (4.65 g), pentafluorophenol (4.2 g), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (4.9 g) and methylene chloride (50 ml) was stirred at room temperature for 18 hours. The reaction solution was washed with water, and the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-hydroxy-3-methoxyphenylacetic acid pentafluorophenyl ester (7.8 g). This product is dissolved in ethyl acetate (80 ml), and thereto is added 3-iodeaniline (7.4 g). The mixture is heated at 60° C. under stirring for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (6.2 g).

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b2a4ac5e1aac4e2bbc9b719031e51886
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Linked notes

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