Benzoyl chloride → (3S)-2-benzoyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 1284450

Reaction equation

HRID 1284450 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][NH:7][C@H:6]([C:13]([OH:15])=[O:14])[CH2:5]2.B([O-])([O-])[O-].[Na+].[Na+].[Na+].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[Na+]>O>[C:23]([N:7]1[C@H:6]([C:13]([OH:15])=[O:14])[CH2:5][C:4]2[C:9](=[CH:10][C:11]([OH:12])=[C:2]([OH:1])[CH:3]=2)[CH2:8]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 159383boric acid, sodium saltHCID 12926159(3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 13935809(3S)-2-benzoyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid [J. Org. Chem., 26, 3533 (1961)] (33.9 g) and sodium borate.10H2O (62 g) are suspended in water (500 ml). Benzoyl chloride (27.5 g) and a solution of sodium hydroxide (13 g) in water (100 ml) are added dropwise to the suspension at 0° C. under stirring. The mixture is stirred at room temperature for 4 hours. The mixture is washed with ethyl acetate, and acidified with conc. HCl, and extracted with ethyl acetate. The extract is dried and distilled to remove the solvent. The crystals are collected by filtration, washed with benzene and then recrystallized from water, whereby (3S)-2-benzoyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (41.7 g) is obtained.

Workup

  1. stirringThe mixture is stirred at room temperature for 4 hours
  2. washThe mixture is washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customThe extract is dried
  5. distillationdistilled
  6. customto remove the solvent
  7. filtrationThe crystals are collected by filtration
  8. washwashed with benzene
  9. customrecrystallized from water

Sources & evidence

ORD record
ord-9bd13a5707174b40aebb5d4118cc000c
Source dataset
uspto-grants-1986_01
Patent number
US04563306

Linked notes

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