HCID 4935483, compound → HCID 11086797, compound

HRID 469702Notes

Reaction equation

HRID 469702 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].[C:19](O[IH]C1C=CC=CC=1[IH]OC(=O)C)(=[O:21])C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1([O:21][CH3:19])[C:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][C:6](=[O:9])[CH:7]=[CH:8]1

Participants

4

Reactant 2

HCID 4935483HCID 4935483, compoundHCID 178476684HCID 178476684, compound

Product 1

HCID 11086797HCID 11086797, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A methanolic (700 mL) solution of compound 2 (29 g, 115 mmol) was cooled in an ice bath before the addition of bis(acetoxyiodo) benzene (62 g, 194 mmol) in six portions over a period of 30 minutes. The solution was stirred in the ice bath for 2 hours then brought to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (1.5 L) and rinsed with water, dilute hydrochloric acid, and brine. The aqueous was back-extracted once with ethyl acetate and the organics combined before drying over anhydrous magnesium sulfate, followed by filtration, and solvent evaporation. The resulting liquid was purified over silica gel using a gradient of ethyl acetate (0 to 2%) in heptane, giving 6.9 g (21%) (3) as a yellow-orange solid. Material was sufficiently pure (approx. 95%) by 1H NMR, which was consistent with that reported in the literature (Synthesis 1998, 775).

Workup

  1. customthen brought to room temperature
  2. washrinsed with water, dilute hydrochloric acid, and brine
  3. extractionThe aqueous was back-extracted once with ethyl acetate
  4. dry with materialbefore drying over anhydrous magnesium sulfate
  5. filtrationfollowed by filtration, and solvent evaporation
  6. customThe resulting liquid was purified over silica gel using a gradient of ethyl acetate (0 to 2%) in heptane

Sources & evidence

ORD record
ord-699592ff992448faa104e892c37d7466
Source dataset
uspto-grants-2014_01
Patent number
US08629164B2

Reaction notes

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