Sodium Hydroxide → HCID 13935817, compound

HRID 1284451Notes

Reaction equation

HRID 1284451 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[C:9]([OH:12])[CH:10]=2)[CH2:5][C@@H:4]([C:14]([O:16]C)=[O:15])[NH:3]1.[OH-].[Na+].B([O-])([O-])[O-].[Na+].[Na+].[Na+]>CO.O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[C:9]([OH:12])[CH:10]=2)[CH2:5][C@@H:4]([C:14]([OH:16])=[O:15])[NH:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159383boric acid, sodium saltHCID 13935815HCID 13935815, compound

Product 1

HCID 13935817HCID 13935817, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl (3S)-1-oxo-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (4 g) is dissolved in methanol (100 ml), and a solution of sodium hydroxide (0.81 g) and sodium borate (7.08 g) in water (100 ml) is added thereto. The mixture is stirred at room temperature overnight. The mixture is distilled under reduced pressure to remove methanol. The residue is acidified with conc.HCl, and the solution is chromatographed on a column (2.6×35 cm) of CHP-20P resin. The column is washed with water (500 ml), and then the product is eluted with 50% methanol. The eluate is distilled under reduced pressure to remove the solvent, and water is added to the residue. The precipitated crystals are collected by filtration and recrystallized from water, whereby (3S)-1-oxo-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (1.81 g) is obtained.

Workup

  1. distillationThe mixture is distilled under reduced pressure
  2. customto remove methanol
  3. customHCl, and the solution is chromatographed on a column (2.6×35 cm) of CHP-20P resin
  4. washThe column is washed with water (500 ml)
  5. washthe product is eluted with 50% methanol
  6. distillationThe eluate is distilled under reduced pressure
  7. customto remove the solvent, and water
  8. additionis added to the residue
  9. filtrationThe precipitated crystals are collected by filtration
  10. customrecrystallized from water

Sources & evidence

ORD record
ord-1fad94a488924a4e88c2ac13ce1deede
Source dataset
uspto-grants-1986_01
Patent number
US04563306

Reaction notes

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