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

HRID 635915Notes

Reaction equation

HRID 635915 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][NH:6][CH2:7][CH2:8][CH:9]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].Br[CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([CH2:7][CH2:8][CH:9]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:25][CH3:26])[CH3:2]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 9948586N-[(4,4-diphenyl)but-3-enyl]glycine ethyl ester

Product 1

HCID 16004947N-[(4,4-diphenyl)but-3-enyl]-N-ethylglycine ethyl esterYield 66.4%

Procedure

A mixture of 0.158 g (0.5 mmol) of N-[(4,4-diphenyl)but-3-enyl]glycine ethyl ester (Compound A26), 0.234 g (2.1 mmol) bromoethane, 0.281 g (2 mmol) potassium carbonate and 0.068 g (0.4 mmol) potassium iodide was stirred under argon for 20 hours at room temperature. The reaction mixture was filtered, the solvent evaporated, and the residue chromatographed on a silica gel column with 20% ethyl acetate in hexanes to yield 0.112 g (66%) N-[(4,4-diphenyl)but-3-enyl]-N-ethylglycine ethyl ester (Compound A16) as an oil. NMR spectra showed: 1H NMR (CDCl3, 300 MHz) 7.60-7.00 (m, 10 H), 6.09 (t, 1 H), 4.13 (q, 2 H), 3.27 (s, 2 H), 2.72 (t, 2 H), 2.61 (q, 2 H), 2.28 (dt, 2 H), 1.23 (t, 3 H), 1.01 (t, 3 H); 13C NMR (CDCl3, 75 MHz) 171.77, 142.96, 142.86, 140.33, 130.09, 128.49, 128.35, 127.48, 127.27, 127.19, 60.58, 54.90, 53.98, 48.20, 28.19, 14.57, 12.70.

Workup

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

Sources & evidence

ORD record
ord-3d16c0a353aa4201893af1305278ee4b
Source dataset
uspto-grants-2001_02
Patent number
US06191165B1

Reaction notes

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