Dimethyl Sulfoxide → HCID 18429304, compound

HRID 1418265Notes

Reaction equation

HRID 1418265 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[C:10]([I:30])=[C:11]([C:17]([I:29])=[C:18]([NH:21][C:22](=[O:28])[CH2:23][O:24]C(=O)C)[C:19]=1[I:20])[CH2:12]CC([O-])=O)=[O:7])(=O)C.C([O:34][CH2:35][CH2:36]Br)(=O)C.C([O-])([O-])=[O:39].[K+].[K+].CS(C)=O.[CH3:48][C:49](N(C)C)=[O:50]>>[OH:24][CH2:23][C:22]([N:21]([CH2:36][CH2:35][OH:34])[C:18]1[C:17]([I:29])=[C:11]([C:10]([I:30])=[C:9]([N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:48][CH2:49][OH:50])[C:19]=1[I:20])[CH2:12][OH:39])=[O:28]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 11430Potassium Carbonate2×HCID 135641-Acetoxy-2-bromoethane2×HCID 31374DimethylacetamideHCID 18429372HCID 18429372, compound

Product 1

HCID 18429304HCID 18429304, compoundYield 33%

Procedure

3,5-Bis(acetoxyacetylamino)-2,4,6-triiodobenzylacetate (190 mg, 0.25 mmol), prepared according to Example 4, was dissolved in dimethylacetamide (5 ml) under an argon atmosphere. 2-Bromoethyl acetate (0.22 ml, 2.0 mmol) and K2CO3 (138 mg, 1.0 mmol) were added. After 16 h, DMSO (1.5 ml), 2-bromoethyl acetate (0.22 ml, 2.0 mmol) and K2CO3 (138 mg, 1.0 mmol) were added and the suspension was stirred for another 24 h. Aqueous NaH2PO4 was added and the resulting solution was extracted with ether (3×25 ml). The combined organic phases were washed with water (4×20 ml) and then dried (MgSO4). The solvent was removed by evaporation and the residue, a colorless oil, was dissolved in a mixture of methanol (3 ml) an 1M aqueous NaOH (3 ml). The solution was stirred for 1 h, pH was adjusted to 6 using aqueous HCl and the solvents were removed by evaporation. Purification by preparative HPLC gave 60 mg (33%) of the product.

Workup

  1. extractionthe resulting solution was extracted with ether (3×25 ml)
  2. washThe combined organic phases were washed with water (4×20 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation
  5. dissolutionthe residue, a colorless oil, was dissolved in a mixture of methanol (3 ml) an 1M aqueous NaOH (3 ml)
  6. stirringThe solution was stirred for 1 h
  7. customthe solvents were removed by evaporation
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-73143401feb748deaefce19ab166c4c4
Source dataset
uspto-grants-1999_03
Patent number
US05882628

Reaction notes

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