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

HRID 635910ノート

反応式

HRID 635910 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5910abb8e75e4867be42ad830a5fb4b8
出典データセット
uspto-grants-2001_02
特許番号
US06191165B1

反応ノート

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