Hydrochloric Acid → Nalpha,Nepsilon-di-(z-15-tetracosenoyl)-L-lysine

HRID 968093Notes

Reaction equation

HRID 968093 reaction equation
C([O:3][C:4](=[O:62])[C@H:5]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:61])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[NH:6][C:7](=[O:31])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])C.[OH-].[Na+].Cl>>[C:7]([NH:6][C@H:5]([C:4]([OH:62])=[O:3])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:61])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])(=[O:31])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9854221HCID 9854221, compound

Product 1

HCID 86595253Nalpha,Nepsilon-di-(z-15-tetracosenoyl)-L-lysine

Procedure

Nα,Nε-di-(z-15-tetracosenoyl)-L-lysine ethyl ester (2 mmol, 1.74 g, prepared according to Example 2) was heated to gentle reflux with 3% methanolic sodium hydroxide solution (25 mL) for 2 hours and left at room temperature overnight. The soapy material was acidified to pH 2 with 1 N cold hydrochloric acid and the white solid was collected and recrystallised from acetone-water (1:1) giving the free acid title compound as a white powder.

Workup

  1. customthe white solid was collected
  2. customrecrystallised from acetone-water (1:1)

Sources & evidence

ORD record
ord-77cea839adef436bad7f25de21566542
Source dataset
uspto-grants-2005_10
Patent number
US06956059B2

Reaction notes

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