Hydroxyphenylacetic acid → 2-(4-Hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl]acetamide

HRID 2119496Notes

Reaction equation

HRID 2119496 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][NH2:17])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](O)=[O:27])=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.O>[OH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([NH:17][CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:10]=2)=[O:27])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2074152-(3-(Benzyloxy)phenyl)ethanamine

Product 1

HCID 234407172-(4-Hydroxyphenyl)-N-{2-[3-(phenylmethoxy)phenyl]ethyl]acetamideYield 56.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[3-(phenylmethoxy)phenyl]ethylamine (2.80 g, 12.3 mmol), 4-hydroxyphenylacetic acid (2.25 g, 14.8 mmol), N,N-diisopropylethylamine (2.79 mL, 16 mmol), and EDCI (3.07 g, 16 mmol) in 20 mL of DMF was stirred at room temperature for 10 h. The reaction mixture was poured into 100 mL of water and the aqueous layer was extracted with CH2Cl2. The organic layer was dried over MgSO4, concentrated, and purified by column chromatography (SiO2, hexanes/ethyl acetate, 1:1) to provide the title compound (2.50 g, 56% yield): ES−MS, (m/z) 362 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. custompurified by column chromatography (SiO2, hexanes/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-7356edbccbde4b9a8e0d3514fdd13766
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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