Hydrochloric Acid → 10-[2-[(3-Carboxy-2,4,6-triiodophenyl)amino]-2-oxoethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid

HRID 2258394Notes

Reaction equation

HRID 2258394 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[C:6]([C:9]1[C:10]([I:33])=[C:11]([NH:17][C:18](=[O:32])[CH2:19][N:20]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:12]([I:16])=[CH:13][C:14]=1[I:15])([OH:8])=[O:7].Cl>O.[OH-].[Na+]>[C:6]([C:9]1[C:10]([I:33])=[C:11]([NH:17][C:18](=[O:32])[CH2:19][N:20]2[CH2:31][CH2:30][N:29]([CH2:2][C:3]([OH:5])=[O:4])[CH2:28][CH2:27][N:26]([CH2:2][C:3]([OH:5])=[O:4])[CH2:25][CH2:24][N:23]([CH2:2][C:3]([OH:5])=[O:4])[CH2:22][CH2:21]2)[C:12]([I:16])=[CH:13][C:14]=1[I:15])([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 22921403N-(3-carboxy-2,4,6-triiodophenyl)-1,4,7,10-tetraazacyclododecane-1-acetamide

Product 1

HCID 1074891610-[2-[(3-Carboxy-2,4,6-triiodophenyl)amino]-2-oxoethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acidYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent3×

Procedure

18.9 g of bromoacetic acid (product available on the market) (0.136 mol) are dissolved in 20 ml of H2O, and by keeping the temperature below 10° C., the solution pH is adjusted to 5 with 68 ml of 2N NaOH (0.136 mol). After adding a solution of 30 g of compound. (B) N-(3-carboxy-2,4,6-triiodophenyl)-1,4,7,10-tetraazacyclododecane-1-acetamide (0.041 mol) in 20.5 ml of 2N NaOH, the reaction mixture is heated at 50° C. for 15 h keeping the pH at 10 with 6.15 ml of 2N NaOH (0.123 mol). A solid precipitates which is then filtered and dissolved in 200 ml of H2O. After acidification of the solution with 82 ml of HCl 2N (0.164 mol) the precipitate is filtered. 28.2 g of 10-[2-[(3-carboxy-2,4,6-triiodophenyl)amino]-2-oxoethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (0.029 mol) are obtained.

Workup

  1. customthe temperature below 10° C.
  2. customA solid precipitates which
  3. filtrationis then filtered
  4. dissolutiondissolved in 200 ml of H2O

Sources & evidence

ORD record
ord-d2da61e57cc64d90bc62943fe6628b6c
Source dataset
uspto-grants-1997_08
Patent number
US05660814

Reaction notes

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