Water → HCID 19348695, compound

HRID 1418162Notes

Reaction equation

HRID 1418162 reaction equation
CC(C)([O-])C.[K+].[C:7]1(=[O:13])[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1.[C:14]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][C:19]=1[NH:26][C:27](=[O:45])[CH2:28][CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]2[O:41][CH2:42][CH2:43][O:44][C:36]=12)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH3:17])([CH3:16])[CH3:15].O>O1CCCC1.CN(C)C=O>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:11]2[C:10](=[O:12])[CH2:9][CH2:8][C:7]2=[O:13])=[CH:20][C:19]=1[NH:26][C:27](=[O:45])[CH2:28][CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]2[O:41][CH2:42][CH2:43][O:44][C:36]=12)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([CH3:15])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 11439SuccinimideHCID 19348758HCID 19348758, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19348695HCID 19348695, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2 ml (2.00 mmol) of a 1M potassium t-butoxide solution in tetrahydrofuran were added to a solution of 200 mg (2.02 mmol) of succinimide in 10 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 15 minutes. A solution of 680 mg (1.35 mmol) of N-[2-t-butyl-5-bromomethylphenyl]-3-(2,3-ethylenedioxyphenyl)octanamide (prepared as described in Preparation 70E) in 5 ml of dimethylformamide was then added to the mixture. The mixture was stirred at room temperature for 1 hour, after which water was added, and the aqueous mixture was extracted with diethyl ether. The extract was washed with 10% v/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium hydrogencarbonate and a with 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 2:3 by volume mixture of hexane and ethyl acetate as the eluent, to give 565 mg of the title compound as a colorless foam-like substance in a 80% yield.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionthe aqueous mixture was extracted with diethyl ether
  3. washThe extract was washed with 10% v/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala with saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through silica gel using a 2:3
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-403b770a76494b919535819396f1bb1d
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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