Hydrochloric Acid → 3-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-4,5-dimethylphenoxymethyl]benzoic Acid

HRID 1866204Notes

Reaction equation

HRID 1866204 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[N:20]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:21]([C:24]2[O:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[C:6]([CH3:34])[CH:5]=1.Cl.C(OCC)(=O)C.O>O1CCOCC1.[OH-].[Na+].CO>[CH3:34][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH2:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=1[N:20]([CH2:30][CH:31]([CH3:33])[CH3:32])[S:21]([C:24]1[O:25][C:26]([CH3:29])=[CH:27][CH:28]=1)(=[O:23])=[O:22])[C:3]([OH:35])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22728543Water ethylacetateHCID 588918933-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-4,5-dimethylphenoxymethyl]benzoic Acid Methyl Ester

Product 1

HCID 102998023-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-4,5-dimethylphenoxymethyl]benzoic AcidYield 91.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]4,5-dimethylphenoxymethyl]benzoic acid methyl ester prepared in Example 1 (850 mg) in dioxane (10 ml), 2N aqueous sodium hydroxide (2.5 ml) and methanol. (4 ml) were added, and the mixture was stirred for 30 hours at room temperature. To the mixture, 2N hydrochloric acid was added, then ethyl acetate-water (30 ml-15 ml) was also added. The organic layer was washed, dried and concentrated under reduced pressure. The residue was dissolved in hot ethanol (40 ml) and added by hot water (40 ml), then allowed to cool. Precipitation was filtrated, and dried to give the title compound (755 mg) having the following physical data.

Workup

  1. addition(4 ml) were added
  2. washThe organic layer was washed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in hot ethanol (40 ml)
  6. additionadded by hot water (40 ml)
  7. temperatureto cool
  8. customPrecipitation
  9. filtrationwas filtrated
  10. customdried

Sources & evidence

ORD record
ord-dfc9a6daa5d0471e897cee06c00fe52f
Source dataset
uspto-grants-2009_12
Patent number
US07629369B2

Reaction notes

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