Cesium carbonate → N,N'-Bis(2,3-dihydroxypropionyl)-N-(2,3-dihydroxypropyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

HRID 1604156Notes

Reaction equation

HRID 1604156 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)[C:20]=2[I:21])[CH2:13]CC([O-])=O)=[O:8])[CH2:4][O:3]1.C([O-])([O-])=[O:36].[Cs+].[Cs+].CC1(C)[O:46][CH:45]([C:47](Cl)=[O:48])[CH2:44][O:43]1>CC(N(C)C)=O.CS(C)=O>[OH:46][CH:45]([CH2:44][OH:43])[C:47]([N:22]([CH2:23][CH:25]([OH:26])[CH2:29][OH:28])[C:19]1[C:18]([I:32])=[C:12]([C:11]([I:33])=[C:10]([NH:9][C:7](=[O:8])[CH:5]([OH:6])[CH2:4][OH:3])[C:20]=1[I:21])[CH2:13][OH:36])=[O:48]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 139748132,2-Dimethyl-1,3-dioxolane-4-carbonyl chlorideHCID 18429246N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate

Product 1

HCID 18429364N,N'-Bis(2,3-dihydroxypropionyl)-N-(2,3-dihydroxypropyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 31374DimethylacetamideSolvent

Procedure

N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate (408 mg, 0.50 mmol) was dissolved in a mixture of dimethylacetamide (4 ml) and DMSO (4 ml) containing Cs2CO3 (1.80 g, 5.52 mmol) and 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid chloride (2.0 ml). After stirring for 8 days, aqueous NaH2PO4 (100 ml) was added and the mixture was extracted with diethyl ether (2×150 ml). The combined organic phases were washed with water (6×100 ml), dried (Na2SO4) and evaporated. The residue was dissolved in a mixture of methanol (10 ml) and water (10 ml) and pH was adjusted to 12 with aqueous NaOH. After stirring for 2 h, concentrated HCl (1.0 ml) was added and stirring was continued for 16 h. After neutralization, the solvents were evaporated and the residue was purified by preparative HPLC. Yield: 149 mg (39%).

Workup

  1. extractionthe mixture was extracted with diethyl 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 residue was dissolved in a mixture of methanol (10 ml) and water (10 ml) and pH
  6. stirringAfter stirring for 2 h
  7. additionconcentrated HCl (1.0 ml) was added
  8. stirringstirring
  9. waitwas continued for 16 h
  10. customAfter neutralization, the solvents were evaporated
  11. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-84a6dd4fcb3549798bb72b361f56160e
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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