Sodium Hydroxide → N-(carboxymethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine

HRID 488296Notes

Reaction equation

HRID 488296 reaction equation
C([O:3][C:4](=[O:42])[CH2:5][N:6]([CH2:36][C:37]([O:39]CC)=[O:38])[C:7](=[O:35])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:12][CH:11]=1)=[O:9])C.[OH-].[Na+]>CO>[C:4]([CH2:5][N:6]([C:7](=[O:35])[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:14][CH:15]=1)=[O:9])[CH2:36][C:37]([OH:39])=[O:38])([OH:42])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091762N-(2-ethoxy-2-oxoethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine ethyl ester

Product 1

HCID 9958748N-(carboxymethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.7 g (1.19 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine ethyl ester and 1.0 ml (6.0 mmol) of 6.0 N NaOH in 75 ml of methanol was stirred at reflux under an argon atmosphere for 4 hours. After removal of the solvent at reduced pressure, the residue was acidified with dilute HCl and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure to a solid which was recrystallized from acetone-hexane to give 0.6 g (95% yield, mp 130°-132°) of N-(carboxymethyl)-N-[2-[4-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine.

Workup

  1. temperatureat reflux under an argon atmosphere for 4 hours
  2. customAfter removal of the solvent at reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated at reduced pressure to a solid which
  6. customwas recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-c86a53e13bbf4b7d8e2d19671eecc998
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

Loading…