Hydrochloric Acid → 3,6-Bis(carboxymethyl)-9-(11-carboxy-1-n-hexylundecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

HRID 1595120Notes

Reaction equation

HRID 1595120 reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([CH2:8][CH2:9][N:10]([CH2:15][CH2:16][N:17]([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:18][C:19]([OH:21])=[O:20])[CH2:11][C:12]([OH:14])=[O:13])[CH2:5][C:4](=[O:28])[O:3]1.C(N(CC)CC)C.[NH2:36][CH:37]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49].Cl>CN(C)C=O.[OH-].[Na+]>[C:19]([CH2:18][N:17]([CH2:16][CH2:15][N:10]([CH2:11][C:12]([OH:14])=[O:13])[CH2:9][CH2:8][N:6]([CH2:7][C:2](=[O:1])[NH:36][CH:37]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[CH2:5][C:4]([OH:28])=[O:3])[CH2:22][C:23]([OH:25])=[O:24])([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 531296112-Aminooctadecanoic acidHCID 15745373N3-(2,6-Dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic Acid

Product 1

HCID 157453803,6-Bis(carboxymethyl)-9-(11-carboxy-1-n-hexylundecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

15.33 g (38 mmol) of N3-(2,6-dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic acid (Example 13a of EP 0 331 616) is suspended in 100 ml of dimethylformamide and mixed in an ice bath with 21.07 ml (152 mmol) of triethylamine and 11.36 g (38 mmol) of 12-aminooctadecanoic acid. After stirring overnight at room temperature, it is concentrated by evaporation in a vacuum, and the residue is absorptively precipitated with 500 ml of diethyl ether. It is suctioned off and the dried reaction product is dissolved in 50 ml of 2 n sodium hydroxide solution. After three hours of stirring, it is neutralized with dilute hydrochloric acid, evaporated to dryness in a vacuum and recrystallized from water. 15.64 g (61% of theory) of a gray powder is obtained.

Workup

  1. concentrationit is concentrated by evaporation in a vacuum
  2. customthe residue is absorptively precipitated with 500 ml of diethyl ether
  3. customthe dried reaction product
  4. stirringAfter three hours of stirring
  5. customevaporated to dryness in a vacuum
  6. customrecrystallized from water
  7. custom15.64 g (61% of theory) of a gray powder is obtained

Sources & evidence

ORD record
ord-2dbbc7458f034e499496061e44ea0af7
Source dataset
uspto-grants-2001_09
Patent number
US06287538B1

Reaction notes

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