Hydrochloric Acid → HCID 22329233, compound

HRID 586878Notes

Reaction equation

HRID 586878 reaction equation
[CH3:1][S:2]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:29]([O:31]C)=[O:30])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH3:1][S:2]([N:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH:26]([CH3:27])[CH3:28])=[CH:18][CH:17]=3)=[CH:15][C:10]=2[CH:9]=[C:8]([C:29]([OH:31])=[O:30])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22328994HCID 22328994, compound

Product 1

HCID 22329233HCID 22329233, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of THF and ethanol (1:1, v/v, 30.0 ml) was dissolved methyl 1-methylsulfonyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (354 mg). To the solution was added 1N sodium hydroxide solution (7.7 ml), and the mixture was stirred at room temperature for 15.5 hours. The mixture was a little concentrated, and to the residue was added 1N hydrochloric acid to convert weakly acidic solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crystals, which were washed with ethyl acetate/hexane to give 1-methylsulfonyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (337 mg, 98%) as white crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give crystals, which
  6. washwere washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-bfd4194753b44236bdf3d84485fb4820
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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