Diisopropylcarbodiimide → N-[2-(3-methoxyphenyl)ethyl]-2-[4-(phenylmethoxy)phenyl]acetamide

HRID 2119456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2119456
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N=C=NC(C)C)(C)C.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:36][CH2:37][NH2:38])[CH:33]=[CH:34][CH:35]=1>CN(C)C=O>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:36][CH2:37][NH:38][C:16](=[O:18])[CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)[CH:33]=[CH:34][CH:35]=1

Komponenten

5

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 748663-MethoxyphenethylamineHCID 810334-Benzyloxyphenylacetic acid

Produkt 1

HCID 12950733N-[2-(3-methoxyphenyl)ethyl]-2-[4-(phenylmethoxy)phenyl]acetamideAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-benzyloxyphenylacetic acid (4.85 g 20 mmol) in dimethylformamide (30 mL) under nitrogen was added 1,3-diisopropylcarbodiimide. After 2 hours, to the solution was added 2-(3-methoxyphenyl)ethylamine (3.02 g, 20 mmol) and stirred at room temperature for 20 hours. The reaction was quenched with a saturated sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 30-70% ethyl acetate/hexane) to provide the title compound (5.74 g, 76% yield): 1H NMR (CDCl3) 7.38 (m, 5H), 7.14 (t, 1H), 7.07 (d, 2H), 6.91 (d, 2H), 6.74 (dd, 1H), 6.62 (m, 2H), 5.37 (br, 1H), 5.06 (s, 2H), 3.77 (s, 3H), 3.47 (s, 2H), 3.44 (t, 2H), 2.70 (t, 2H); ES−MS (m/z) 376 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with a saturated sodium carbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 30-70% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d26a48d3379846fc8ab418771912cb58
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06686351B2

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