Triethylamine → N-(2-ethoxy-2-oxoethyl)-N-[3-[3-(3-nitrophenoxy)propoxy]-5-(octadecyloxy)benzoyl]glycine ethyl ester

HRID 488263Notes

Reaction equation

HRID 488263 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:20]=1)[C:15](O)=[O:16])([O-:3])=[O:2].[NH:43]([CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46].C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH2:54]([O:53][C:51](=[O:52])[CH2:50][N:43]([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:15](=[O:16])[C:14]1[CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:20]=[C:12]([O:11][CH2:10][CH2:9][CH2:8][O:7][C:6]2[CH:40]=[CH:41][CH:42]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:13]=1)[CH3:55]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 80502Diethyl iminodiacetateHCID 190917603-[3-(3-Nitrophenoxy)propoxy]-5-(octadecyloxy)benzoic acid

Product 1

HCID 19091825N-(2-ethoxy-2-oxoethyl)-N-[3-[3-(3-nitrophenoxy)propoxy]-5-(octadecyloxy)benzoyl]glycine ethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 4.0 g (6.83 mmol) of 3-[3-(3-nitrophenoxy)propoxy]-5-(octadecyloxy)benzoic acid in 65 ml of thionyl chloride was stirred at reflux for 2.5 hours. The excess thionyl chloride was removed at reduced pressure and the residual solid acid chloride was dissolved in 75 ml of methylene chloride and added dropwise to a stirred, ice bath cooled solution of 1.5 ml of diethyl iminodiacetate (8.5 mmol) and 1.9 ml (13.7 mmol) of triethylamine in 25 ml of methylene chloride. The reaction mixture was stirred in the cooling bath for 30 minutes, at room temperature for 20 hours and then was washed with NaHCO3 solution. The dried organic layer was concentrated at reduced pressure to an oil which was purified by HPLC using 25% ethyl acetate-hexane to give 4.32 g (84% yield) of N-(2-ethoxy-2-oxoethyl)-N-[3-[3-(3-nitrophenoxy)propoxy]-5-(octadecyloxy)benzoyl]glycine ethyl ester as an oil. The structure was confirmed by the nmr and mass spectra.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe excess thionyl chloride was removed at reduced pressure
  3. dissolutionthe residual solid acid chloride was dissolved in 75 ml of methylene chloride
  4. additionadded dropwise to a stirred, ice bath
  5. washwas washed with NaHCO3 solution
  6. concentrationThe dried organic layer was concentrated at reduced pressure to an oil which
  7. customwas purified by HPLC

Sources & evidence

ORD record
ord-4ae3c543355b48f080450bf8915831dd
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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