Sodium Hydroxide → N-(carboxymethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine

HRID 488286Notes

Reaction equation

HRID 488286 reaction equation
C([O:3][C:4](=[O:53])[CH2:5][N:6]([CH2:47][C:48]([O:50]CC)=[O:49])[C:7](=[O:46])[C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:11]=[C:10]([NH:30][C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:9]=1)C.[OH-].[Na+]>CO>[C:4]([CH2:5][N:6]([C:7](=[O:46])[C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:11]=[C:10]([NH:30][C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:9]=1)[CH2:47][C:48]([OH:50])=[O:49])([OH:53])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19091780N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine ethyl ester

Product 1

HCID 19091836N-(carboxymethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycineYield 79.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.1 g (2.8 mmol) of N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine ethyl ester and 2.35 ml (14 mmol) of 6N NaOH in 75 ml of methanol was stirred at reflux for 5 hours under an argon atmosphere. The solvent was removed at reduced pressure and the residue was acidified. The product was extracted with ethyl acetate and the dried extract was concentrated to a solid which was recrystallized from acetonitrile to give 1.54 g (79% yield, mp 109°-111°) of N-(carboxymethyl)-N-[3,5-bis(1-oxotetradecylamino)benzoyl]glycine.

Workup

  1. temperatureat reflux for 5 hours under an argon atmosphere
  2. customThe solvent was removed at reduced pressure
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated to a solid which
  6. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-21fb594454654cb4bea909c707662094
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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