Benzyl chloroformate → Methyl [4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetate

HRID 1506671

Reaction equation

HRID 1506671 reaction equation
[CH:1]1[C:2]([CH2:19][C:20]([OH:22])=[O:21])=[CH:3][C:4]([I:18])=[C:5]([O:8][C:9]2[CH:10]=[C:11]([I:17])[C:12]([OH:16])=[C:13]([I:15])[CH:14]=2)[C:6]=1[I:7].[CH2:23](OC(Cl)=O)C1C=CC=CC=1>CO>[CH3:23][O:21][C:20](=[O:22])[CH2:19][C:2]1[CH:1]=[C:6]([I:7])[C:5]([O:8][C:9]2[CH:10]=[C:11]([I:17])[C:12]([OH:16])=[C:13]([I:15])[CH:14]=2)=[C:4]([I:18])[CH:3]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 65552Tetraiodothyroacetic acid

Product 1

HCID 52919069Methyl [4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]acetateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In anhydrous conditions, Tetrac (1.0 g, 1.3 mmol, 1.0 eq.) was suspended in MeOH (20 mL). TEA (181.4 μL, 1.3 mmol, 1.0 eq.) was then added dropwise followed by benzylchloroformate 184.8 μL, 1.3 mmol, 1.0 eq.). After stirring for 30 minutes, the solution was filtered, the solvent was removed from the residue and the product was separated by silica gel chromatography (eluent=DCM). The collected fractions were then evaporated to give a white powder which was recrystallized to give orange crystals (990 mg, 1.3 mmol) of methyl-2-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)acetate in a quantitative yield.

Workup

  1. filtrationthe solution was filtered
  2. customthe solvent was removed from the residue
  3. customthe product was separated by silica gel chromatography (eluent=DCM)
  4. customThe collected fractions were then evaporated
  5. customto give a white powder which
  6. customwas recrystallized

Sources & evidence

ORD record
ord-ae207d11d4da41d7a53128e7242aef87
Source dataset
uspto-grants-2015_12
Patent number
US09220788B2

Linked notes

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