Sodium Hydroxide → HCID 22048284, compound

HRID 1833253Notes

Reaction equation

HRID 1833253 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([C:19](=[O:31])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH:27]([CH2:29][CH3:30])[CH3:28])[CH:21]=2)=[N:7][CH:6]=1.[OH-].[Na+]>CO>[CH:27]([O:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[C:19]([C:8]1[C:9]2[C:14](=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[C:5]([CH2:4][C:3]([OH:32])=[O:2])=[CH:6][N:7]=1)=[O:31])([CH2:29][CH3:30])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69551004HCID 69551004, compound

Product 1

HCID 22048284HCID 22048284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of [1-(3-sec-butoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid methyl ester (170 mg, 0.39 mmol) in methanol (3.5 mL) was added 1.0 N sodium hydroxide solution (2.0 mL, 1.56 mmol). The reaction mixture was heated at 90° C. for 1 h, concentrated in vacuo and diluted with water (3 mL). The aqueous phase was extracted with diethyl ether (1×10) and then acidified to pH=4 by addition of 1N hydrogen chloride solution. The aqueous phase was then extracted with dichloromethane (3×15 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo. HPLC purification afforded [1-(3-sec-butoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetic acid trfluoroacetic acid salt (59 mg, 36% yield) as a light yellow solid. HR-MS m/e calcd for C24H15N1O6 (M−H+) 424.1755, found 424.1758; 1H NMR (300 MHz) compatible.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water (3 mL)
  3. extractionThe aqueous phase was extracted with diethyl ether (1×10)
  4. additionacidified to pH=4 by addition of 1N hydrogen chloride solution
  5. extractionThe aqueous phase was then extracted with dichloromethane (3×15 mL)
  6. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customHPLC purification

Sources & evidence

ORD record
ord-683628605f334c27a88ddd9f24a2bad2
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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