Methyl iodide → N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propy-4-methoxycarbonylphenoxy)-alpha-methyl-3,4-methylenedioxyphenylacetamide

HRID 1378849Notes

Reaction equation

HRID 1378849 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14](=[O:39])[CH:15]([C:30]2[CH:35]=[CH:34][C:33]3[O:36][CH2:37][O:38][C:32]=3[CH:31]=2)[O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:18]=2[CH2:27][CH2:28][CH3:29])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:40][Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].IC>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14](=[O:39])[C:15]([C:30]2[CH:35]=[CH:34][C:33]3[O:36][CH2:37][O:38][C:32]=3[CH:31]=2)([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:18]=2[CH2:27][CH2:28][CH3:29])[CH3:40])(=[O:12])=[O:11])=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 15383771N-(4-iso-propylbenzenesulfonyl)-alpha-(4-carbomethoxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamideHCID 86588160Lithim bis(trimethylsilylamide)

Product 1

HCID 19080425N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propy-4-methoxycarbonylphenoxy)-alpha-methyl-3,4-methylenedioxyphenylacetamideYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.516 g (0.93 mmol) of the product of Example 57 dissolved in 1.0 mL of anhydrous THF was added 2.80 mL (2.80 mmol) of a 1.0M solution of lithim bis(trimethylsilylamide) in THF at -78° C. under a nitrogen atmosphere. The reaction mixture was magnetically stirred at -78° C. for 1 hour, then 174 μL (2.80 mmol) of iodomethane was added via syringe. The reaction was allowed to warm to room temperature and was stirred an additional 14 hours. The reaction was next quenched with excess 10% aqueous NaHSO4 and partitioned between EtOAc and water. The organic layer was washed with saturated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with CHCl3 --MeOH--NH4OH (90:10:1). Evaporation of the purified fractions and drying in vacuo afforded 0.293 g (55%) of the title compound as an amorphous solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred an additional 14 hours
  3. customThe reaction was next quenched with excess 10% aqueous NaHSO4
  4. custompartitioned between EtOAc and water
  5. washThe organic layer was washed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with CHCl3 --MeOH--NH4OH (90:10:1)
  11. customEvaporation of the purified fractions
  12. customdrying in vacuo

Sources & evidence

ORD record
ord-4fb625ff0df640e7abb75bc455f83a17
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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