Reaction #1543035

Reaction equation

water

1.5-bis(2,6-dioxomorpholino)-3-carboxymethyl-3-azapentane

triethylamine

11-aminoundecanoic acid ethyl ester

→

title compound

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

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe solution is heated for 3 hours to 70° C.
2. 2
   Otherthe solution is evaporated to dryness in a vacuum
3. 3
   workup.ADDITIONthe solution is mixed by drops with concentrated hydrochloric acid until permanent cloudiness
4. 4
   workup.STIRRINGAfter stirring overnight in the ice bath
5. 5
   Washwashed with water
6. 6
   Otherdried in a vacuum at 50° 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.

Source