Water → 3,6-Bis(carboxymethyl)-9-(10-carbethoxydecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

HRID 1595121Notes

Reaction equation

HRID 1595121 reaction equation
[O:1]=[C:2]1[CH2:7][N:6]([CH2:8][CH2:9][N:10]([CH2:21][C:22]([OH:24])=[O:23])[CH2:11][CH2:12][N:13]2[CH2:18][C:17](=[O:19])[O:16][C:15](=[O:20])[CH2:14]2)[CH2:5][C:4](=[O:25])[O:3]1.[OH2:26].C(N(CC)CC)C.[CH2:34]([O:36][C:37](=[O:49])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][NH2:48])[CH3:35]>CN(C)C=O>[C:15]([CH2:14][N:13]([CH2:12][CH2:11][N:10]([CH2:21][C:22]([OH:24])=[O:23])[CH2:9][CH2:8][N:6]([CH2:7][C:2](=[O:1])[NH:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][C:37]([O:36][CH2:34][CH3:35])=[O:49])[CH2:5][C:4]([OH:3])=[O:25])[CH2:18][C:17]([OH:16])=[O:19])([OH:20])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 100825DTPA dianhydrideHCID 13192100Ethyl 11-aminoundecanoate

Product 1

HCID 102109193,6-Bis(carboxymethyl)-9-(10-carbethoxydecylcarbamoylmethyl)-3,6,9-triazaundecanedioic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

17.85 g (50 mmol) of 1.5-bis(2,6-dioxomorpholino)-3-carboxymethyl-3-azapentane is stirred in 200 ml of dimethylformamide and mixed with 9 ml (50 mmol) of water. The solution is heated for 3 hours to 70° C., cooled off to 0° C. and 36.07 ml (260 mmol) of triethylamine and 10.8 g (50 mmol) of 11-aminoundecanoic acid ethyl ester are added. After stirring overnight at room temperature, the solution is evaporated to dryness in a vacuum. The residue is taken up in 100 ml of water and the solution is mixed by drops with concentrated hydrochloric acid until permanent cloudiness. After stirring overnight in the ice bath, the finely crystalline precipitate is suctioned off, washed with water and dried in a vacuum at 50° C. 14.9 g (65% of theory) of the title compound is obtained as a white powder with melting point 155-157° C.

Workup

  1. temperatureThe solution is heated for 3 hours to 70° C.
  2. customthe solution is evaporated to dryness in a vacuum
  3. additionthe solution is mixed by drops with concentrated hydrochloric acid until permanent cloudiness
  4. stirringAfter stirring overnight in the ice bath
  5. washwashed with water
  6. customdried in a vacuum at 50° C

Sources & evidence

ORD record
ord-ea93700c73294cd3b6a5ef84aa352f98
Source dataset
uspto-grants-2001_09
Patent number
US06287538B1

Reaction notes

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