N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamide → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-formyl-2-n-propylphenoxy)-3,4-methylenedioxyphenyl-acetamide

HRID 865530Notes

Reaction equation

HRID 865530 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14](=[O:37])[CH:15]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]=[O:24])=[CH:19][C:18]=2[CH2:25][CH2:26][CH3:27])(=[O:11])=[O:12])=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 19080393N-(4-iso-propylbenzenesulfonyl)-alpha-(4-formyl-2-n-propylphenoxy)-3,4-methylenedioxyphenyl-acetamideYield 26.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.573 g (1.09 mmol) of the product of Example 65 dissolved in 5.0 mL of dichloromethane was added 2.86 g (32.9 mmol) of manganese dioxide and 1.15 g of finely powdered 3A molecular sieves and the reaction mixture was magnetically stirred at room temperature for 14 hours. The reaction mixture was then filtered through a bed of celite and MgSO4 and the flitrate was evaporated in vacuo. The residue was dissolved in dichloromethane and applied to a silica gel flash chromatography column and then eluted with 3% MeOH--CH2Cl2. Evaporation of the purified fractions and drying in vacuo afforded 0.149 g (26%) of the title compound.

Workup

  1. filtrationThe reaction mixture was then filtered through a bed of celite and MgSO4
  2. customthe flitrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washeluted with 3% MeOH
  5. customEvaporation of the purified fractions
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-58a61b3fe8b4400591ba990f1f392190
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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