Sodium Methoxide → 7-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 409244Notes

Reaction equation

HRID 409244 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17][N:18]([CH2:29][C:30]([O:32][CH3:33])=[O:31])S(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>CO>[CH3:33][O:32][C:30]([C:29]1[N:18]=[CH:17][C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][CH:8]=[C:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:6]=2)=[O:31]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 671108664-Benzyl-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester

Product 1

HCID 671101307-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl esterYield 48.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of crude 4-benzyl-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester (1.54 g) in methanol (1.75 mL) was added a solution of NaOMe (30 wt %) in methanol (1.75 mL) with stirring. After stirring for 5 h at ambient temperature the mixture was concentrated in vacuo and water (20 mL) was added. The pH of the mixture was adjusted to 7 to 8 by addition of 6N hydrochloric acid before the mixture was extracted with ethyl acetate (2×25 mL). The combined organic phases were then dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using hexanes:ethyl acetate=7:3 as the eluent to give the title compound as an off-white solid (451 mg); MS-(+)-ion: M+1=294.0.

Workup

  1. stirringAfter stirring for 5 h at ambient temperature the mixture
  2. concentrationwas concentrated in vacuo and water (20 mL)
  3. additionwas added
  4. additionThe pH of the mixture was adjusted to 7 to 8 by addition of 6N hydrochloric acid before the mixture
  5. extractionwas extracted with ethyl acetate (2×25 mL)
  6. dry with materialThe combined organic phases were then dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-0633429dced54fddb2e1612a0658494d
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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