Sodium Hydroxide → HCID 19091758, compound

HRID 488300Notes

Reaction equation

HRID 488300 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][CH:13]=[C:12]([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:11]=1)=[O:9])C.[OH-].[Na+]>CO>[C:4]([CH2:5][N:6]([C:7](=[O:35])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([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:11]=1)=[O:9])[CH2:36][C:37]([OH:39])=[O:38])([OH:42])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091837HCID 19091837, compound

Product 1

HCID 19091758HCID 19091758, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.3 g (2.2 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[2-[3-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine ethyl ester and 1.8 ml (11 mmol) of 6N NaOH in 100 ml of methanol was stirred at reflux under argon for 3 hours. The solvent was removed at reduced pressure, the residue was acidified 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 1.08 g (91% yield, mp 126°-128°) of N-(carboxymethyl)-N-[2-[3-(octadecyloxy)phenyl]-1,2-dioxoethyl]glycine.

Workup

  1. temperatureat reflux under argon for 3 hours
  2. customThe solvent was removed 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-86dc07f6a3b54c63b5f1c9a59e012031
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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