Sodium Hydroxide → N-(carboxymethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine

HRID 488281Notes

Reaction equation

HRID 488281 reaction equation
C[O:2][C:3](=[O:49])[CH2:4][N:5]([CH2:44][C:45]([O:47]C)=[O:46])[C:6](=[O:43])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:9]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:8]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:45]([CH2:44][N:5]([C:6](=[O:43])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:9]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:8]=1)[CH2:4][C:3]([OH:49])=[O:2])([OH:47])=[O:46]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19091769N-(2-methoxy-2-oxoethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine methyl ester

Product 1

HCID 19091803N-(carboxymethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycineYield 59.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.90 g (1.3 mmol) of N-(2-methoxy-2-oxoethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine methyl ester and 1.0 ml (6 mmol) of 6N NaOH in 80 ml of methanol and 35 ml of dioxane was stirred at reflux for 6 hours. The solvents were removed at reduced pressure, the residue was acidified and the product was removed by filtration. Recrystallization from ethyl acetate-hexane gave 0.51 g (59% yield, mp 84°-87° ) of N-(carboxymethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe solvents were removed at reduced pressure
  3. customthe product was removed by filtration
  4. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-36c5e1bf83024caabe841b91ef15088d
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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