Potassium Iodide → HCID 90281985, compound

HRID 1497521Notes

Reaction equation

HRID 1497521 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[NH2:16][C:17]1[CH:29]=[CH:28][C:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[C:24]([O:23][C:21]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][CH2:2][C:3]2[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=2)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:29][CH:28]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 22456708tert-Butyl 3-(chloromethyl)benzoate

Product 1

HCID 90281985HCID 90281985, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 3-(chloromethyl)benzoate (500 mg) in N,N-dimethylformamide (10.0 mL) were added tert-butyl 4-aminobenzoate (426 mg), potassium carbonate (610 mg), and potassium iodide (36.6 mg), followed by stirring at 60° C. overnight. To the reaction suspension was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 3-({[4-(tert-butoxycarbonyl)phenyl]amino}methyl)benzoate (671 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-bc7b3714def04d51a66758cecd8ab3b9
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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