HCID 19348758, compound → HCID 19348797, compound

HRID 1637468Notes

Reaction equation

HRID 1637468 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][C:18]=1[NH:25][C:26](=[O:44])[CH2:27][CH:28]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]2[O:40][CH2:41][CH2:42][O:43][C:35]=12)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O.O>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:19][C:18]=1[NH:25][C:26](=[O:44])[CH2:27][CH:28]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]2[O:40][CH2:41][CH2:42][O:43][C:35]=12)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 19348758HCID 19348758, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19348797HCID 19348797, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

138 mg (0.745 mmol) of potassium phthalimide were added to a solution of 288 mg (0.573 mmol) of N-[2-t-butyl-5-bromomethyl-phenyl]-3-(2,3-ethylenedioxyphenyl)octanamide (prepared as described in Preparation 70E) in 5 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was diluted with water and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 295 mg (yield 91%) of the title compound as a colorless foam-like substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialafter which it was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel using a 3:1
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-fdee7dd10d68437ead38f82960130daa
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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