Methanol → Acetic acid ({3-chlorocarbonyl-5-[(2,3-dihydroxy-propyl)-methyl-carbamoyl]-2,4,6-triiodo-phenyl}-methyl-carbamoyl)-methyl ester

HRID 2188502Notes

Reaction equation

HRID 2188502 reaction equation
Cl[C:2]([C:4]1[C:5]([I:24])=[C:6]([N:15]([CH3:23])[C:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])=[O:17])[C:7]([I:14])=[C:8]([C:11]([Cl:13])=[O:12])[C:9]=1[I:10])=[O:3].[CH:25]([OH:29])(O)[CH2:26][CH3:27].C[OH:31].C[C:33]([N:35](C)C)=O>C(OCC)(=O)C>[Cl:13][C:11]([C:8]1[C:7]([I:14])=[C:6]([N:15]([CH3:23])[C:16]([CH2:18][O:19][C:20](=[O:22])[CH3:21])=[O:17])[C:5]([I:24])=[C:4]([C:2](=[O:3])[N:35]([CH2:27][CH:26]([OH:31])[CH2:25][OH:29])[CH3:33])[C:9]=1[I:10])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 31374DimethylacetamideHCID 134919PropanediolHCID 53903191HCID 53903191, compound

Product 1

HCID 59470601Acetic acid ({3-chlorocarbonyl-5-[(2,3-dihydroxy-propyl)-methyl-carbamoyl]-2,4,6-triiodo-phenyl}-methyl-carbamoyl)-methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl ester (16.25 g, 22.9 mmol) and 3-methylamino-1,2,-propanediol (4.42 ml, 45.8 mmol) were stirred in DMA (80 ml) for 72 hours at room temperature. The mixture was diluted with ethyl acetate (150 ml) and washed with ice water/brine (50:50, 20 ml×3). The organics were collected, dried over MgSO4, filtered and evaporated to dryness. The product was purified by silica column chromatography eluting with DCM: methanol to give acetic acid ({3-chlorocarbonyl-5-[(2,3-dihydroxy-propyl)-methyl-carbamoyl]-2,4,6-triiodo-phenyl}-methyl-carbamoyl)-methyl ester (5.42 g, 6.96 mmol).

Workup

  1. washwashed with ice water/brine (50:50, 20 ml×3)
  2. customThe organics were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe product was purified by silica column chromatography
  7. washeluting with DCM

Sources & evidence

ORD record
ord-107fce388cf748348d45b60809b1b599
Source dataset
uspto-grants-2012_12
Patent number
US08323619B2

Reaction notes

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