Hydrochloric Acid → alpha-(2-n-Propyl-4-methylaminosulfonylphenoxy)-3,4-methylenedioxyphenylacetic acid

HRID 865535Notes

Reaction equation

HRID 865535 reaction equation
[CH2:1]([C:4]1[CH:24]=[C:23]([S:25]([NH:28][CH3:29])(=[O:27])=[O:26])[CH:22]=[CH:21][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:8]([O:10]C)=[O:9])[CH2:2][CH3:3].[OH-].[Na+].C(Cl)(Cl)Cl.CO.[NH4+].[OH-].Cl>CO.C1COCC1.ClCCl>[CH2:1]([C:4]1[CH:24]=[C:23]([S:25]([NH:28][CH3:29])(=[O:27])=[O:26])[CH:22]=[CH:21][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][C:15]2[O:18][CH2:19][O:20][C:14]=2[CH:13]=1)[C:8]([OH:10])=[O:9])[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 19080392Methyl alpha-(2-n-propyl-4-methylaminosulfonylphenoxy)-3,4-methylenedioxyphenylacetateHCID 21873181Chloroform methanol ammonium hydroxide

Product 1

HCID 19080383alpha-(2-n-Propyl-4-methylaminosulfonylphenoxy)-3,4-methylenedioxyphenylacetic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.372 g (0.884 mmol) of the product of Step D dissolved in 3.0 mL of methanol was added 212 μL (1.06 mmol) of a 5.0N aqueous sodium hydroxide solution which resulted in a cloudy suspension. The reaction was warmed to assist solution, methanol (1 mL) was added followed by dichloromethane (0.5 mL), however a clear solution was not obtained. Additional 5N sodium hydroxide solution was added (212 μL), and finally 0.5 mL of THF was added which resulted in a clear solution. After stirring an additional 15 hours at room temperature, TLC analysis (CHCl3 -MeOH-NH4OH 80:15:1) indicated complete hydrolysis of the starting material and the reaction was adjusted to pH=7 with 6N HCl. The reaction mixture was then concentrated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH-HOAc (92:7:1). Combination of the purified fractions and drying in vacuo afforded 0.335 g (93%) of the title compound as an amorphous solid.

Workup

  1. customresulted in a cloudy suspension
  2. temperatureThe reaction was warmed
  3. additionwas added
  4. customhowever a clear solution was not obtained
  5. additionwas added which
  6. customresulted in a clear solution
  7. customhydrolysis of the starting material
  8. concentrationThe reaction mixture was then concentrated in vacuo
  9. customthe residue was purified on a silica gel flash chromatography column
  10. washeluted with CHCl3 -MeOH-HOAc (92:7:1)
  11. customCombination of the purified fractions and drying in vacuo

Sources & evidence

ORD record
ord-73f6729e87204ebf921871ae6b787f00
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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