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

HRID 1358031Notes

Reaction equation

HRID 1358031 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-f84a1df06b384815b075edf85212b74a
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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