Sodium Hydroxide → HCID 22329107, compound

HRID 586864Notes

Reaction equation

HRID 586864 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:22][CH2:21][C:20]([C:28]([O:30]C)=[O:29])=[CH:19][C:18]=3[CH:32]=2)=[CH:10][CH:9]=1)[CH3:2].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([S:24]([CH3:27])(=[O:25])=[O:26])[CH2:22][CH2:21][C:20]([C:28]([OH:30])=[O:29])=[CH:19][C:18]=3[CH:32]=2)=[CH:12][CH:13]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 17824786HCID 17824786, compound

Product 1

HCID 22329107HCID 22329107, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In methanol (25 ml) and THF (25 ml) was dissolved methyl 7-[4-(3-ethoxypropoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.22 g). To the solution was added 1N sodium hydroxide solution (5 ml), and the mixture was stirred at room temperature overnight and concentrated. To the residue was added water, and the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated to give 7-[4-(3-ethoxypropoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.23 g) as pale yellow crystals.

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-774af6aa401547f68aee963a54f1cb3c
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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