Sodium Hydroxide → HCID 69522003, compound

HRID 856629Notes

Reaction equation

HRID 856629 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:23][CH2:22][C:21]([C:29]([O:31]C)=[O:30])=[CH:20][C:19]=3[CH:33]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.O>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([S:25]([CH3:28])(=[O:27])=[O:26])[CH2:23][CH2:22][C:21]([C:29]([OH:31])=[O:30])=[CH:20][C:19]=3[CH:33]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22938394HCID 22938394, compound

Product 1

HCID 69522003HCID 69522003, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl 7-[4-(2-butoxyethoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.94 g) in THF-water (20-20 ml) was added 1N aqueous solution of sodium hydroxide (8.0 ml) at room temperature and the mixture was stirred for 20 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and to the residue was added 1N hydrochloric acid (10 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the precipitated crystals were collected by filtration. The crystals were washed with diisopropylether, to give 7-[4-(2-butoxyethoxy)phenyl]-1-methanesulfonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (1.23 g) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added 1N hydrochloric acid (10 ml)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe precipitated crystals were collected by filtration
  8. washThe crystals were washed with diisopropylether

Sources & evidence

ORD record
ord-c41a34ff834249d5a68e35d28aa04a13
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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