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