Potassium Iodide → N-[(4,4-diphenyl)but-3-enyl]glycine ethyl ester

HRID 635910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 635910
Br[CH2:2][CH2:3][CH:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH2:24])[CH3:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][NH:24][CH2:2][CH2:3][CH:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:20]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 104017744,4-Diphenyl-3-butenyl bromide

Produkt 1

HCID 9948586N-[(4,4-diphenyl)but-3-enyl]glycine ethyl esterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5.95 g (20.7 mmol) 4-bromo-1,1-diphenyl-1-butene (prepared as described in F. A. Ali et al., J. Med. Chem. 28: 653-660, 1985), 4.71 g (33.7 mmol) glycine ethyl ester hydrochloride (Aldrich, Milwaukee, Wis.), 11.62 g (84 mmol) potassium carbonate and 1.06 g (6.38 mmol) potassium iodide in 50 ml acetonitrile was refluxed with stirring under argon for seven hours. The reaction mixture was filtered, the solvent evaporated and the residue chromatographed on silica gel column with 20% ethyl acetate in hexanes to give 3.70 g (yield 58%) of N-[(4,4-diphenyl)but-3-enyl]glycine ethyl ester (compound A26) as an oil. NMR spectra of the product showed: 1H NMR (CDCl3, 300 MHz) 7.60-7.00 (m, 10 H), 6.09 (t, 1 H), 4.16 (q, 2 H), 3.35 (s, 2 H), 2.71 (t, 2 H), 2.32 (dt, 2 H), 1.25 (t, 3 H), 13C NMR (CDCl3, 75 MHz) 172.29, 143.25, 142.37, 139.82, 129.72, 128.13, 128.04, 127.97, 127.13, 126.92, 126.88, 126.68, 60.56, 50.73, 49.32, 30.33, 14.14.

Aufarbeitung

  1. customprepared
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent evaporated
  4. customthe residue chromatographed on silica gel column with 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5910abb8e75e4867be42ad830a5fb4b8
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06191165B1

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