Reaction #1509612

Reaction equation

compound

2-(6,9-Bisethoxycarbonylmethyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-3-yl)pentanedioic acid diethyl ester

sodium hydroxide

→

2-(6,9-Biscarboxymethyl-3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-3-yl)pentanedioic acid

Yield 60.0%

Solvents

water

ethanol

Conditions

Workup

1. 1
   Temperatureto reflux for 24 h
2. 2
   workup.ADDITIONby adding weakly acidic resin
3. 3
   FiltrationThe resin is filtered off
4. 4
   Washwashed with water
5. 5
   workup.ADDITIONA strongly basic resin is added to the filtrate
6. 6
   Filtrationfiltered off
7. 7
   Washwashed twice with water
8. 8
   WashThe product is eluted with 50% acetic acid
9. 9
   OtherAfter evaporation to dryness
10. 10
    Otherthe product is obtained in the form of brown crystals

Procedure

15 mg of the compound obtained in stage 2 (26.5 μmol) are dissolved in 40 μl of ethanol and 53 μl of 5N sodium hydroxide are added dropwise rapidly. The mixture is brought to reflux for 24 h. The reaction medium is diluted 10-fold with water and the pH is then adjusted to 6.5 by adding weakly acidic resin. The resin is filtered off and washed with water. A strongly basic resin is added to the filtrate and then filtered off and washed twice with water. The product is eluted with 50% acetic acid. After evaporation to dryness, the product is obtained in the form of brown crystals. m=8 mg. Yield=60%.

Source