Sodium Hydroxide → N-(3,5-dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 411744Notes

Reaction equation

HRID 411744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:21]([C:22]([O:24]C)=[O:23])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:21]([C:22]([OH:24])=[O:23])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86586601N-(3,5-dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester

Product 1

HCID 18541314N-(3,5-dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-(3,5-Dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, methyl ester (100 mg, 0.25 mmol) was dissolved in 0.625 mL of MeOH and 0.625 mL of a 0.4 N solution of NaOH in MeOH was added. The resulting mixture was stirred overnight at rt. Volatiles were removed in vacuo and the residue was partitioned between 5% citric acid and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2X). The combined organic extracts were washed with brine, and dried over anhydrous Na2SO4. The residue obtained after filtration and evaporation of volatiles was purified by flash column chromatography on silica gel eluted with mixtures of CH2Cl2 and MeOH to afford N-(3,5 -dichlorobenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (85 mg) as a white foam, homogeneous by TLC (9:1 CH2Cl2:MeOH)

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was partitioned between 5% citric acid and CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2X)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe residue obtained
  7. filtrationafter filtration and evaporation of volatiles
  8. customwas purified by flash column chromatography on silica gel
  9. washeluted with mixtures of CH2Cl2 and MeOH

Sources & evidence

ORD record
ord-aa7c34a306594c94bc8acb6f77165d8e
Source dataset
uspto-grants-2003_05
Patent number
US06559174B2

Reaction notes

Loading…