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

HRID 635910Notes

Reaction equation

HRID 635910 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5910abb8e75e4867be42ad830a5fb4b8
Source dataset
uspto-grants-2001_02
Patent number
US06191165B1

Reaction notes

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