Tetrabutylammonium Fluoride → N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamide

HRID 865529Notes

Reaction equation

HRID 865529 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:44])[CH:15]([C:35]2[CH:40]=[CH:39][C:38]3[O:41][CH2:42][O:43][C:37]=3[CH:36]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][O:24][Si](C(C)(C)C)(C)C)=[CH:19][C:18]=2[CH2:32][CH2:33][CH3:34])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14](=[O:44])[CH:15]([C:35]2[CH:40]=[CH:39][C:38]3[O:41][CH2:42][O:43][C:37]=3[CH:36]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][C:18]=2[CH2:32][CH2:33][CH3:34])(=[O:11])=[O:12])=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 19080371N-(4-iso-propylbenzenesulfonyl)-alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

Product 1

HCID 19080378N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamideYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3.20 g (5.01 mmol) of the product of Step D dissolved in 5.0 mL of anhydrous THF was added 5.06 mL (5.06 mmol) of a 1.0 M solution of tetrabutylammonium fluoride in THF and the reaction mixture was stirred at room temperature under a nitrogen atmosphere. After 2.5 hours 1.0 mL additional tetrabutylammonium fluoride in THF was added and the reaction mixture was stirred for an additional 14 hours. The reaction mixture was then concentrated in vacuo and applied to a silica gel flash chromatography column and eluted with 60% EtOAc-hexane. Combination of the purified fractions and drying in vacuo afforded 0.691 g (26%) of the title compound as an amorphous powder.

Workup

  1. stirringthe reaction mixture was stirred for an additional 14 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. washeluted with 60% EtOAc-hexane
  4. customCombination of the purified fractions and drying in vacuo

Sources & evidence

ORD record
ord-389f9cfaef6e4c74bbc9559a2c122cf2
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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