Sodium Hydroxide → HCID 19091792, compound

HRID 488253Notes

Reaction equation

HRID 488253 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][N:6]([CH2:35][C:36]([O:38]CC)=[O:37])[C:7](=[O:34])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:33])[CH2:16][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][CH3:32])[CH:9]=1)C.[OH-].[Na+]>CO>[C:36]([CH2:35][N:6]([C:7](=[O:34])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:33])[CH2:16][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][CH3:32])[CH:9]=1)[CH2:5][C:4]([OH:41])=[O:3])([OH:38])=[O:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091782HCID 19091782, compound

Product 1

HCID 19091792HCID 19091792, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.0 g (5.2 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[3-(1-oxooctadecylamino)benzoyl]glycine ethyl ester and 25 ml (25 mmol) of 1N NaOH in 100 ml of methanol was stirred at reflux for 6 hours. The solvent was removed at reduced pressure, the residue was acidified and the precipitate was filtered and recrystallized from ethyl acetate-hexane to give 2.0 g (74% yield, mp 132°-142° ) of N-(carboxymethyl)-N-[3-(1-oxooctadecylamino)benzoyl]glycine.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvent was removed at reduced pressure
  3. filtrationthe precipitate was filtered
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fab34d54627245c1a0264917feb5b016
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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