Methanol → HCID 59470601, compound

HRID 219498

Reaction equation

HRID 219498 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 59470601HCID 59470601, compound

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-9de2866bb0c1419ca7946ef3cf685deb
Source dataset
uspto-grants-2012_06
Patent number
US08202511B2

Linked notes

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