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

HRID 635910노트

반응식

HRID 635910 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5910abb8e75e4867be42ad830a5fb4b8
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191165B1

반응 노트

불러오는 중…