Potassium Carbonate → N,N'-Bis(2,3-dihydroxypropionyl)-N,N'-bis(2-hydroxyethyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

HRID 1418272Notes

Reaction equation

HRID 1418272 reaction equation
CC1(C)[O:6][CH:5]([C:7]([NH:9][C:10]2[C:11]([I:33])=[C:12]([C:18]([I:32])=[C:19]([NH:22][C:23]([CH:25]3[CH2:29][O:28]C(C)(C)[O:26]3)=[O:24])[C:20]=2[I:21])[CH2:13]CC([O-])=O)=[O:8])[CH2:4][O:3]1.C([O-])([O-])=[O:36].[K+].[K+].C([O:44][CH2:45][CH2:46]Br)(=O)C.[CH3:48][C:49](N(C)C)=[O:50]>CS(C)=O>[OH:6][CH:5]([CH2:4][OH:3])[C:7]([N:9]([CH2:46][CH2:45][OH:44])[C:10]1[C:11]([I:33])=[C:12]([C:18]([I:32])=[C:19]([N:22]([C:23](=[O:24])[CH:25]([OH:26])[CH2:29][OH:28])[CH2:48][CH2:49][OH:50])[C:20]=1[I:21])[CH2:13][OH:36])=[O:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 31374DimethylacetamideHCID 18429246N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate

Product 1

HCID 18362191N,N'-Bis(2,3-dihydroxypropionyl)-N,N'-bis(2-hydroxyethyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate (204 mg, 0.25 mmol) was dissolved in a mixture of dimethylacetamide (5 ml) and DMSO (1.5 ml) containing K2CO3 (276 mg, 2.0 mmol) and 2-bromoethyl acetate (0.44 ml, 4.0 mmol). After stirring for 48 h, an aqueous NaH2PO4 buffer was added and the mixture was extracted with ether (2×150 ml). The combined organic phases were washed with water (6×100 ml), dried (Na2SO4) and evaporated. The solid residue was dissolved in a mixture of methanol (12 ml) and water (12 ml) and the pH was adjusted to 12 with aqueous NaOH. After stirring for 18 h, the solution was acidified with concentrated HCl (0.70 ml) and stirring was continued for 3 h. The solution was neutralized and the solvents were removed by evaporation. The product was purified by preparative HPLC. Yield: 98 mg (50%).

Workup

  1. extractionthe mixture was extracted with ether (2×150 ml)
  2. washThe combined organic phases were washed with water (6×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. dissolutionThe solid residue was dissolved in a mixture of methanol (12 ml) and water (12 ml)
  6. stirringAfter stirring for 18 h
  7. stirringstirring
  8. waitwas continued for 3 h
  9. customthe solvents were removed by evaporation
  10. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-929f8704f87d4936831decf7cc383cb7
Source dataset
uspto-grants-1999_03
Patent number
US05882628

Reaction notes

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