HCID 59309441, compound → HCID 57583234, compound

HRID 1645495Notes

Reaction equation

HRID 1645495 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[C:8]([I:19])=[C:9]([C:13]([I:18])=[C:14]([NH2:17])[C:15]=1[I:16])[C:10]([Cl:12])=[O:11])=[O:6])[CH:2]=[CH2:3].[C:20]([OH:23])(=[O:22])[CH3:21].[C:24]([OH:27])(=[O:26])[CH3:25].[C:28]([OH:31])(=[O:30])[CH3:29].[O:32]=[C:33](Cl)[C@H:34]([C@@H:36]([CH2:38]O)O)O>CC(N(C)C)=O.C(OCC)(=O)C>[C:20]([O:23][CH:36]([CH2:38][O:30][C:28](=[O:31])[CH3:29])[CH:34]([O:26][C:24](=[O:27])[CH3:25])[C:33](=[O:32])[NH:17][C:14]1[C:13]([I:18])=[C:9]([C:10]([Cl:12])=[O:11])[C:8]([I:19])=[C:7]([C:5](=[O:6])[NH:4][CH2:1][CH:2]=[CH2:3])[C:15]=1[I:16])(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 59309441HCID 59309441, compoundHCID 131729479HCID 131729479, compound

Product 1

HCID 57583234HCID 57583234, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

3-Allylcarbamoyl-5-amino-2,4,6-triiodo-benzoyl chloride (7) (20 g, 32.4 mmol) was dissolved in dry DMA (50 mL) and threonic acid chloride triacetate (18) (18.22 g, 64.8 mmol) was added. The reaction was stirred for 3 days at room temperature with nitrogen bubbling through. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with ice-water (5×20 mL). The organics were collected, dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The solid was adsorbed onto silica gel and purified by column chromatography eluting with DCM: ethyl acetate (0-100%, SiO2, 750 g, 10 CV) to give acetic acid 2,3-diacetoxy-1-(3-allylcarbamoyl-5-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-propyl ester as a yellow solid (15.1 g, 54%).

Workup

  1. washwashed with ice-water (5×20 mL)
  2. customThe organics were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. custompurified by column chromatography
  7. washeluting with DCM

Sources & evidence

ORD record
ord-f35d0905833b483fa6fb95046eca097c
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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