Sodium Hydroxide → 2-[2-(4-methoxyphenyl)sulfonyl-3,4-dihydro-1H-isoquinolin-1-yl]acetic Acid

HRID 1642148Notes

Reaction equation

HRID 1642148 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]2[CH2:24][C:25]([O:27]C)=[O:26])(=[O:13])=[O:12])=[CH:7][CH:6]=1>C1COCC1.O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]2[CH2:24][C:25]([OH:27])=[O:26])(=[O:13])=[O:12])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66756190HCID 66756190, compound

Product 1

HCID 52638012-[2-(4-methoxyphenyl)sulfonyl-3,4-dihydro-1H-isoquinolin-1-yl]acetic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 6 M aqueous NaOH solution was added to a mixture of methyl 2-(2-(4-methoxyphenylsulfonyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)acetate (15.22 g, 40.54 mmol) in THF (200 ml) and water (120 ml), and stirring was carried out overnight at room temperature. The solvent was then removed under reduced pressure, and a 6 M aqueous HCl solution (125 ml) and DCM (400 ml) were added. The phases were separated and then the organic phase was washed with concentrated NaCl solution, dried over sodium sulfate and concentrated. Yield: 14.65 g (100%)

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additiona 6 M aqueous HCl solution (125 ml) and DCM (400 ml) were added
  3. customThe phases were separated
  4. washthe organic phase was washed with concentrated NaCl solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03c334f4b2cc4e72bb6c7095db810294
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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