Triethylamine → 3,6-Bis(carboxymethyl)-9-(10-carboxydecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

HRID 412989Notes

Reaction equation

HRID 412989 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][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48]>CN(C)C=O>[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][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[CH2:5][C:4]([OH:28])=[O:3])[CH2:22][C:23]([OH:25])=[O:24])([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1708311-Aminoundecanoic acidHCID 15745373N3-(2,6-Dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic Acid

Product 1

HCID 157453743,6-Bis(carboxymethyl)-9-(10-carboxydecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.33 g (38 mmol) of N3-(2,6-dioxomorpholinoethyl)-N6-(ethoxy-carbonylmethyl)-3,6-diazaoctanedioic acid (Example 13a of EP 0331 616) is suspended in dimethylformamide (DMF) and mixed in an ice bath with 21.07 ml (152 mmol) of triethylamine and 7.65 g (38 mmol) of 11-aminoundecanoic acid. The temperature is allowed to increase to room temperature and the reaction solution is stirred overnight. After completion of the reaction, the possibly still slightly cloudy solution is filtered and the filtrate is concentrated by evaporation in a vacuum. The residue is absorptively precipitated with ether and then recrystallized from water (17.8 g). The ethyl ester is dissolved in 2 N NaOH and is adjusted to pH 7 after 3 hours by adding Amberlite® IR 120 (H+). The ion exchange material is suctioned off, the filtrate is freeze-dried (20.1 g) and then added to H2O/methanol (2:1) on 100 ml of Amberlite® IR 120 (H+) and the acid eluate is concentrated by evaporation and recrystallized from water.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe possibly still slightly cloudy solution is filtered
  3. concentrationthe filtrate is concentrated by evaporation in a vacuum
  4. customThe residue is absorptively precipitated with ether
  5. customrecrystallized from water (17.8 g)
  6. dissolutionThe ethyl ester is dissolved in 2 N NaOH
  7. waitis adjusted to pH 7 after 3 hours
  8. additionby adding Amberlite® IR 120 (H+)
  9. customthe filtrate is freeze-dried (20.1 g)
  10. additionadded to H2O/methanol (2:1) on 100 ml of Amberlite® IR 120 (H+)
  11. concentrationthe acid eluate is concentrated by evaporation
  12. customrecrystallized from water

Sources & evidence

ORD record
ord-fac1897d9a0a4a3dbe9964e34e360d43
Source dataset
uspto-grants-2003_05
Patent number
US06565830B1

Reaction notes

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