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

HRID 488287Notes

Reaction equation

HRID 488287 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:59])[CH2:7][N:8]([CH2:53][C:54]([O:56]CC)=[O:55])[C:9](=[O:52])[C:10]1[CH:15]=[C:14]([NH:16][C:17](=[O:33])[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:13]=[C:12]([NH:34][C:35](=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:11]=1)C>>[C:6]([CH2:7][N:8]([C:9](=[O:52])[C:10]1[CH:15]=[C:14]([NH:16][C:17](=[O:33])[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:13]=[C:12]([NH:34][C:35](=[O:51])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:11]=1)[CH2:53][C:54]([OH:56])=[O:55])([OH:59])=[O:5]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 19091838N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine ethyl ester

Product 1

HCID 19091757N-(carboxymethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine

Procedure

Sodium hydroxide hydrolysis of N-(2-ethoxy-2-oxoethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine ethyl ester as in Example 56 and recrystallization from methanol-water gave N-(carboxymethyl)-N-[3,5-bis(1-oxohexadecylamino)benzoyl]glycine, mp 129°-133°.

Workup

  1. customas in Example 56 and recrystallization from methanol-water

Sources & evidence

ORD record
ord-6edd69e216da4d009484ad75c8ee23ae
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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