Potassium Iodide → HCID 86663433, compound

HRID 446518Notes

Reaction equation

HRID 446518 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH2:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C.[I-].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:12][C:13]1[CH:25]=[CH:24][C:16]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[CH:15][CH:14]=1)[CH3:11]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 117544Ethyl 6-bromohexanoateHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 86663433HCID 86663433, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 6-bromohexanoate (8.44 mL, 49.7 mmol) and tert-butyl 4-aminobenzoate (6.41 g, 33.2 mmol) were dissolved in N,N-dimethylformamide (33 mL), N,N-diisopropylethylamine (8.64 mL, 49.7 mmol) was added, and the mixture was stirred at 50° C. for 3 days. Potassium iodide (8.25 g, 49.7 mmol) was added, and the mixture was further stirred at 50° C. for 4 days. A saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate (×2). The resulting organic layer was washed with water (×3) and saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1, v/v). A mixed solvent of hexane and dichloromethane was added to the resulting white solid, and the mixture was filtered to give the title compound (5.54 g; yield, 50%) as a white solid.

Workup

  1. stirringthe mixture was further stirred at 50° C. for 4 days
  2. extractionthe mixture was extracted with ethyl acetate (×2)
  3. washThe resulting organic layer was washed with water (×3) and saturated sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1, v/v)
  7. additionA mixed solvent of hexane and dichloromethane was added to the resulting white solid
  8. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-5bc2ba3e62874422a613cd0ed680f793
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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